메뉴 건너뛰기




Volumn 35, Issue 3, 2005, Pages 483-491

A cheap, simple, and versatile method for acetylation of alcohols and phenols and selective deprotection of aromatic acetates under solvent-free condition

Author keywords

Acetylation; Alcohols; Deprotection; Phenols; Solvent free

Indexed keywords

ACETIC ACID; ACETIC ACID DERIVATIVE; ACYCLIC HYDROCARBON SUBSTITUENT; ALCOHOL DERIVATIVE; AROMATIC COMPOUND; LITHIUM DERIVATIVE; PHENOL DERIVATIVE; SODIUM HYDROXIDE; SOLVENT;

EID: 14644420947     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200048988     Document Type: Article
Times cited : (12)

References (49)
  • 4
    • 0035808956 scopus 로고    scopus 로고
    • A mild procedure for rapid and selective deprotection of aryl acetates using natural kaolinitic clay as a reusable catalyst
    • Bandgar, B. P.; Uppalla, L. S.; Sagar, A. D.; Sadavarte, V. S. A mild procedure for rapid and selective deprotection of aryl acetates using natural kaolinitic clay as a reusable catalyst. Tetrahedron Lett. 2001, 42, 1163-1165.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1163-1165
    • Bandgar, B.P.1    Uppalla, L.S.2    Sagar, A.D.3    Sadavarte, V.S.4
  • 5
    • 37049106282 scopus 로고
    • 4-Dialkylaminopyridines: Super acylation and alkylation catalysts
    • Scriven, E. F. V. 4-Dialkylaminopyridines: super acylation and alkylation catalysts. Chem. Soc. Rev. 1983, 12, 129-161.
    • (1983) Chem. Soc. Rev. , vol.12 , pp. 129-161
    • Scriven, E.F.V.1
  • 6
    • 80051729483 scopus 로고
    • Tributylphosphine: A remarkable acylation catalyst
    • Vedejs, E.; Diver, S. T. Tributylphosphine: A remarkable acylation catalyst. J. Am. Chem. Soc. 1993, 115, 3358-3359.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3358-3359
    • Vedejs, E.1    Diver, S.T.2
  • 7
    • 0001702869 scopus 로고    scopus 로고
    • Dual activation in the esterification of hindered alcohols with anhydrides using MgBr2 and a tertiary amine
    • Vedejs, E.; Daugulis, O. Dual activation in the esterification of hindered alcohols with anhydrides using MgBr2 and a tertiary amine. J. Org. Chem. 1996, 61, 5702-5703.
    • (1996) J. Org. Chem. , vol.61 , pp. 5702-5703
    • Vedejs, E.1    Daugulis, O.2
  • 8
    • 0035817170 scopus 로고    scopus 로고
    • 3 is an efficient solid support reagent for the acetylation of amines, alcohols, and phenols
    • 3 is an efficient solid support reagent for the acetylation of amines, alcohols, and phenols. Tetrahedron 2001, 57, 7047-7051.
    • (2001) Tetrahedron , vol.57 , pp. 7047-7051
    • Veejendra, K.1    Yadav, K.2    Babu, G.3    Mittal, M.4
  • 9
    • 0344950837 scopus 로고    scopus 로고
    • Superbase-promoted acylation of hindered alcohols
    • D'Sa, B. A.; Verkade, J. G. Superbase-promoted acylation of hindered alcohols. J. Org. Chem. 1996, 61, 2963-2966.
    • (1996) J. Org. Chem. , vol.61 , pp. 2963-2966
    • D'Sa, B.A.1    Verkade, J.G.2
  • 10
    • 0001516761 scopus 로고    scopus 로고
    • Selective monoacetylation of unsymmetrical diols catalyzed by silica gel-supported sodium hydrogen sulfate
    • Berton, G. W. Selective monoacetylation of unsymmetrical diols catalyzed by silica gel-supported sodium hydrogen sulfate. J. Org. Chem. 1997 (62), 8952-8954.
    • (1997) J. Org. Chem. , Issue.62 , pp. 8952-8954
    • Berton, G.W.1
  • 12
    • 0000073239 scopus 로고    scopus 로고
    • An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethane sulfonate
    • Procopiou, A. P.; Baugh, D. P. S.; Falck, S. S.; Inglis, A. G. G. An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethane sulfonate. J. Org. Chem. 1998, 63, 2342-2347.
    • (1998) J. Org. Chem. , vol.63 , pp. 2342-2347
    • Procopiou, A.P.1    Baugh, D.P.S.2    Falck, S.S.3    Inglis, A.G.G.4
  • 13
    • 33751391774 scopus 로고
    • Cobalt (II) chloride catalyzed acylation of alcohols with acetic anhydride
    • Iqbal, J.; Srivastava, R. R. Cobalt (II) chloride catalyzed acylation of alcohols with acetic anhydride. J. Org. Chem. 1992, 57, 2001-2007.
    • (1992) J. Org. Chem. , vol.57 , pp. 2001-2007
    • Iqbal, J.1    Srivastava, R.R.2
  • 14
    • 0003002340 scopus 로고    scopus 로고
    • 4-Dialkylaminopyridines: Super acylation and alkylation catalysts
    • Li, A.-X.; Li, T.-S.; Ding, T.-H. 4-Dialkylaminopyridines: Super acylation and alkylation catalysts. Chem. Commun. 1997, 1389-1390.
    • (1997) Chem. Commun. , pp. 1389-1390
    • Li, A.-X.1    Li, T.-S.2    Ding, T.-H.3
  • 15
    • 0012615648 scopus 로고    scopus 로고
    • Scandium trifluoromethane sulfonate as an exteremly active Lewis acid catalyst in acylation of alcohols with acid anhydride and mixed anhydride
    • Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. Scandium trifluoromethane sulfonate as an exteremly active Lewis acid catalyst in acylation of alcohols with acid anhydride and mixed anhydride. J. Org. Chem. 1996, 61, 4560.
    • (1996) J. Org. Chem. , vol.61 , pp. 4560
    • Ishihara, K.1    Kubota, M.2    Kurihara, H.3    Yamamoto, H.4
  • 16
    • 0033605890 scopus 로고    scopus 로고
    • An efficient method for acylation reaction
    • Saravanan, P.; Singh, V. K. An efficient method for acylation reaction. Tetrahedron Lett. 1999, 40, 2611-2614.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2611-2614
    • Saravanan, P.1    Singh, V.K.2
  • 17
    • 0032753189 scopus 로고    scopus 로고
    • Indium triflate: An efficient catalyst for acylation reactions
    • Chauhan, K. K.; Frost, C. G.; Love, I.; Waite, D. Indium triflate: an efficient catalyst for acylation reactions. Synlett 1999, 1743-1744.
    • (1999) Synlett , pp. 1743-1744
    • Chauhan, K.K.1    Frost, C.G.2    Love, I.3    Waite, D.4
  • 18
    • 0037940236 scopus 로고    scopus 로고
    • Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions
    • Karimi, B.; Maleki, J. Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions. J. Org. Chem. 2003, 68, 4951-4954.
    • (2003) J. Org. Chem. , vol.68 , pp. 4951-4954
    • Karimi, B.1    Maleki, J.2
  • 19
    • 0002661787 scopus 로고    scopus 로고
    • Scandium(III) or lanthanide(III) triflates as recyclable catalysts for the direct acetylation of alcohols with acetic acid
    • Barrett, A. G.M.; Braddock, D. C. Scandium(III) or lanthanide(III) triflates as recyclable catalysts for the direct acetylation of alcohols with acetic acid. Chem. Commun. 1997, 351.
    • (1997) Chem. Commun. , pp. 351
    • Barrett, A.G.M.1    Braddock, D.C.2
  • 20
    • 0002433425 scopus 로고
    • An efficient esterification reaction between equimolar amounts of free carboxylic acids and alcohols by the combined use of octamethylcyclotetrasiloxane and a catalytic amount of titanium(IV) chloride tris(trifluoromethanesulfonate)
    • Izumi, J.; Shiina, I.; Mukaiyama, T. An efficient esterification reaction between equimolar amounts of free carboxylic acids and alcohols by the combined use of octamethylcyclotetrasiloxane and a catalytic amount of titanium(IV) chloride tris(trifluoromethanesulfonate). Chem. Lett. 1995, 141-142.
    • (1995) Chem. Lett. , pp. 141-142
    • Izumi, J.1    Shiina, I.2    Mukaiyama, T.3
  • 21
    • 0024453914 scopus 로고
    • The diethylisopropylsilyl group: A new protecting group for alcohols
    • Toshima, K.; Mukaiyama, S.; Kinoshita, M.; Tatsuta, K. The diethylisopropylsilyl group: A new protecting group for alcohols. Tetrahedron Lett. 1989, 30, 6413-6416.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6413-6416
    • Toshima, K.1    Mukaiyama, S.2    Kinoshita, M.3    Tatsuta, K.4
  • 22
    • 0002414880 scopus 로고    scopus 로고
    • A new scandium complex as an extremely active acylation catalyst
    • Ishihara, K.; Kubota, M.; Yammamoto, H. A new scandium complex as an extremely active acylation catalyst. Synlett 1996, 265-266.
    • (1996) Synlett , pp. 265-266
    • Ishihara, K.1    Kubota, M.2    Yammamoto, H.3
  • 24
    • 0036039105 scopus 로고    scopus 로고
    • 2 solid acid catalyst for acylation of alcohols and phenols
    • 2 solid acid catalyst for acylation of alcohols and phenols. Synth. Commun. 2002, 32, 2815-2819.
    • (2002) Synth. Commun. , vol.32 , pp. 2815-2819
    • Reddy, B.1    Sreekanth, P.M.2
  • 26
    • 0032555553 scopus 로고    scopus 로고
    • Lipase-catalysed chemoselective monoacetylation of hydroxyalkylphenols and chemoselective removal of a single acetyl group from their diacetates
    • Allevi, P.; Ciuffreda, P.; Longo, A.; Anastasia, M. Lipase-catalysed chemoselective monoacetylation of hydroxyalkylphenols and chemoselective removal of a single acetyl group from their diacetates. Tetrahedron: Asymmetry 1998, 9, 2915-2924.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2915-2924
    • Allevi, P.1    Ciuffreda, P.2    Longo, A.3    Anastasia, M.4
  • 28
    • 0000466390 scopus 로고    scopus 로고
    • Iodine: A versatile reagent in carbohydrate chemistry IV. Per-O-acetylation, regioselective acylation and acetolysis
    • Kartha, K. P.R.; Field, R. A. Iodine: A versatile reagent in carbohydrate chemistry IV. Per-O-acetylation, regioselective acylation and acetolysis. Tetrahedron 1997, 53, 11753-11766.
    • (1997) Tetrahedron , vol.53 , pp. 11753-11766
    • Kartha, K.P.R.1    Field, R.A.2
  • 29
    • 0032507928 scopus 로고    scopus 로고
    • Microwave-promoted lipase-catalyzed reactions
    • Lin, G.; Lin, W. Y. Microwave-promoted lipase-catalyzed reactions. Tetrahedron Lett. 1998, 39, 4333-4336.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4333-4336
    • Lin, G.1    Lin, W.Y.2
  • 30
    • 0032514503 scopus 로고    scopus 로고
    • Zeolite HSZ-360 as a new reusable catalyst for the direct acylation of alcohols and phenols under solventless condition
    • Ballini, R.; Bosica, G.; Carloni, S.; Ciaralli, L.; Maggi, R.; Sartori, G. Zeolite HSZ-360 as a new reusable catalyst for the direct acylation of alcohols and phenols under solventless condition. Tetrahedron Lett. 1998, 39, 6049-6052.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6049-6052
    • Ballini, R.1    Bosica, G.2    Carloni, S.3    Ciaralli, L.4    Maggi, R.5    Sartori, G.6
  • 31
    • 0001738245 scopus 로고    scopus 로고
    • Twisted amides as selective acylating agents for hydroxygroups under neutral conditions
    • Yamada, S.; Sugaki, T.; Matsuzaki, K. Twisted amides as selective acylating agents for hydroxygroups under neutral conditions. J. Org. Chem. 1996, 61, 5932-5938.
    • (1996) J. Org. Chem. , vol.61 , pp. 5932-5938
    • Yamada, S.1    Sugaki, T.2    Matsuzaki, K.3
  • 32
    • 0001526323 scopus 로고    scopus 로고
    • Enantioselective acylations catalyzed by chiral phosphines
    • Vedejs, E.; Daugulis, O.; Diver, S. T. Enantioselective acylations catalyzed by chiral phosphines. J. Org. Chem. 1996, 61, 430-431.
    • (1996) J. Org. Chem. , vol.61 , pp. 430-431
    • Vedejs, E.1    Daugulis, O.2    Diver, S.T.3
  • 34
    • 0037013838 scopus 로고    scopus 로고
    • 2O-Py/basic alumina as a versatile reagent for acylation in solvent-free conditions under microwave irradiation
    • 2O-Py/basic alumina as a versatile reagent for acylation in solvent-free conditions under microwave irradiation. Tetrahedron Lett. 2002, 43, 4261-4265.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4261-4265
    • Paul, S.1    Nanda, P.2    Gupta, R.3    Loupy, A.4
  • 35
    • 0033520227 scopus 로고    scopus 로고
    • Microwave activation in phase transfer catalyst
    • For review
    • Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J. L.; Petit, A. Microwave activation in phase transfer catalyst. Tetrahedron 1999, 55, 10851-10870For review see:.
    • (1999) Tetrahedron , vol.55 , pp. 10851-10870
    • Deshayes, S.1    Liagre, M.2    Loupy, A.3    Luche, J.L.4    Petit, A.5
  • 36
    • 0035813244 scopus 로고    scopus 로고
    • Microwave assisted organic synthesis: A review
    • Lidstrom, P.; Tiereney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis: a review. Tetrahedron 2001, 57, 9225-9283.
    • (2001) Tetrahedron , vol.57 , pp. 9225-9283
    • Lidstrom, P.1    Tiereney, J.2    Wathey, B.3    Westman, J.4
  • 37
    • 0037450938 scopus 로고    scopus 로고
    • Rapid synthesis of substituted 5-phenyl-1,3-dioxan-4-ones under microwave-induced solvent-free conditions
    • Ferrett, R. R.; Hyde, M. J.; Lahti, K. A.; Friebe, T. L. Rapid synthesis of substituted 5-phenyl-1,3-dioxan-4-ones under microwave-induced solvent-free conditions. Tetrahedron Lett. 2003, 44, 2573-2576.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2573-2576
    • Ferrett, R.R.1    Hyde, M.J.2    Lahti, K.A.3    Friebe, T.L.4
  • 38
    • 0000333337 scopus 로고    scopus 로고
    • Microwave-assisted solid-phase synthesis of 5-carboxamido-N- acetyltryptamine derivatives
    • Finaru, A.; Berthault, A.; Besson, T.; Guillaumet, G.; Berteina-Raboin, S. Microwave-assisted solid-phase synthesis of 5-carboxamido-N-acetyltryptamine derivatives. Org. Lett. 2002, 4, 2613-2615.
    • (2002) Org. Lett. , vol.4 , pp. 2613-2615
    • Finaru, A.1    Berthault, A.2    Besson, T.3    Guillaumet, G.4    Berteina-Raboin, S.5
  • 39
    • 0348048824 scopus 로고    scopus 로고
    • Microwave assisted solvent-free amination of halo-(pyridine or pyrimidine) without transition metal catalyst
    • Narayan, S.; Seelhammer, T.; Gawley, R. E. Microwave assisted solvent-free amination of halo-(pyridine or pyrimidine) without transition metal catalyst. Tetrahedron Lett. 2004, 45, 757-759.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 757-759
    • Narayan, S.1    Seelhammer, T.2    Gawley, R.E.3
  • 40
    • 0036033009 scopus 로고    scopus 로고
    • The rapid synthesis of β-nitrostyrenes under microwave irradiation without solvent
    • Wang, C.; Wang, S. The rapid synthesis of β-nitrostyrenes under microwave irradiation without solvent. Synth. Commun. 2002, 32, 3481-3486.
    • (2002) Synth. Commun. , vol.32 , pp. 3481-3486
    • Wang, C.1    Wang, S.2
  • 42
    • 0035981570 scopus 로고    scopus 로고
    • Silylation of hydroxy groups with HMDS under microwave irradiation and solvent-free conditions
    • Mojtahedi, M. M.; Saidi, M. R.; Bolourtchian, M.; Heravi, M. M. Silylation of hydroxy groups with HMDS under microwave irradiation and solvent-free conditions. Phosphorus, Sulfur, and Silicon 2002, 177, 289-292.
    • (2002) Phosphorus, Sulfur, and Silicon , vol.177 , pp. 289-292
    • Mojtahedi, M.M.1    Saidi, M.R.2    Bolourtchian, M.3    Heravi, M.M.4
  • 43
    • 0033438891 scopus 로고    scopus 로고
    • Microwave assisted deprotection of trimethylsilyl ethers under solvent-free conditions catalyzed by clay or a palladium complex
    • Mojtahedi, M. M.; Saidi, M. R.; Heravi, M. M.; Bolourtchian, M. Microwave assisted deprotection of trimethylsilyl ethers under solvent-free conditions catalyzed by clay or a palladium complex. Monash. Chem. 1999, 130, 1175-1178.
    • (1999) Monash. Chem. , vol.130 , pp. 1175-1178
    • Mojtahedi, M.M.1    Saidi, M.R.2    Heravi, M.M.3    Bolourtchian, M.4
  • 44
    • 0344256698 scopus 로고    scopus 로고
    • A new protocol for O-methylation of phenolic compounds with trimethyl phosphite or trimethyl phosphate under solvent-free condition and microwave irradiation
    • Saidi, M. R.; Rajabi, F. A new protocol for O-methylation of phenolic compounds with trimethyl phosphite or trimethyl phosphate under solvent-free condition and microwave irradiation. Phosphorus, Sulfur, and Silicon 2003, 178, 2343-2348.
    • (2003) Phosphorus, Sulfur, and Silicon , vol.178 , pp. 2343-2348
    • Saidi, M.R.1    Rajabi, F.2
  • 45
    • 0344110866 scopus 로고
    • Preparation of 2-alkyl-1-naphthols and 1-alkyl-2-naphthols
    • Saidi, M. R. Preparation of 2-alkyl-1-naphthols and 1-alkyl-2-naphthols. Indian J. Chem. 1982 (21B), 474-475.
    • (1982) Indian J. Chem. , Issue.21 B , pp. 474-475
    • Saidi, M.R.1
  • 46
    • 0033524812 scopus 로고    scopus 로고
    • Microwave irradiation techniques for the Cannizzaro reaction
    • Sharifi, A.; Mojtahedi, M. M.; Saidi, M. R. Microwave irradiation techniques for the Cannizzaro reaction. Tetrahedron Lett. 1999, 38, 1179-1180.
    • (1999) Tetrahedron Lett. , vol.38 , pp. 1179-1180
    • Sharifi, A.1    Mojtahedi, M.M.2    Saidi, M.R.3
  • 48
    • 0344738557 scopus 로고    scopus 로고
    • Lithium perchlorate-catalyzed three-component coupling: A facile and general method for the synthesis of α-aminophosphonates under solvent-free conditions
    • Azizi, N.; Saidi, M. R. Lithium perchlorate-catalyzed three-component coupling: A facile and general method for the synthesis of α- aminophosphonates under solvent-free conditions. Eur. J. Org. Chem. 2003b, 4630.
    • (2003) Eur. J. Org. Chem. , pp. 4630
    • Azizi, N.1    Saidi, M.R.2
  • 49
    • 0043210612 scopus 로고    scopus 로고
    • Synthesis of tertiary α-amino phosphonate by one-pot three-component coupling mediated by LPDE
    • Azizi, N.; Saidi, M. R. Synthesis of tertiary α-amino phosphonate by one-pot three-component coupling mediated by LPDE. Tetrahedron 2003c, 59, 5329-5332.
    • (2003) Tetrahedron , vol.59 , pp. 5329-5332
    • Azizi, N.1    Saidi, M.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.