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Volumn , Issue 13, 2008, Pages 1993-1998

Microwave-assisted cleavage of aryl methyl ethers with lithium thioethoxide (LiSEt)

Author keywords

Demethylation; Lithium; Microwave irradiation; Phenol protecting groups; SN2 reactions; Thioethanolate

Indexed keywords

LITHIUM DERIVATIVE; LITHIUM THIOETHOXIDE; MERCAPTAMINE;

EID: 49749105279     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077949     Document Type: Article
Times cited : (20)

References (92)
  • 2
    • 0003405157 scopus 로고    scopus 로고
    • 3rd ed, Georg Thieme Verlag: Stuttgart
    • (b) Kocienski, P. J. Protecting Groups, 3rd ed.; Georg Thieme Verlag: Stuttgart, 2004,.
    • (2004) Protecting Groups
    • Kocienski, P.J.1
  • 67
    • 49749087757 scopus 로고    scopus 로고
    • PhD Dissertation; TU-Berlin: Germany
    • (a) Geller, T. PhD Dissertation; TU-Berlin: Germany, 1998.
    • (1998)
    • Geller, T.1
  • 73
    • 31544444465 scopus 로고    scopus 로고
    • For an efficient entry to stilbene 5 by cross-metathesis, see
    • For an efficient entry to stilbene 5 by cross-metathesis, see: Velder, J.; Ritter, S.; Lex, J.; Schmalz, H.-G. Synthesis 2006, 273.
    • (2006) Synthesis , pp. 273
    • Velder, J.1    Ritter, S.2    Lex, J.3    Schmalz, H.-G.4
  • 79
    • 0037774706 scopus 로고    scopus 로고
    • For a review on colchicine total synthesis, see: (a) Graening, T.; Schmalz, H.-G. Angew. Chem. Int. Ed. 2003, 42, 2580; Angew. Chem. 2003, 115, 2684.
    • For a review on colchicine total synthesis, see: (a) Graening, T.; Schmalz, H.-G. Angew. Chem. Int. Ed. 2003, 42, 2580; Angew. Chem. 2003, 115, 2684.
  • 81
    • 0019955048 scopus 로고    scopus 로고
    • For previous examples of selective O-demethylation reactions with thiolate-based reagents which, however, require harsh reaction conditions, long reaction times and/or the use of HMPT as a toxic additive, see: (a) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1982, 47, 1831.
    • For previous examples of selective O-demethylation reactions with thiolate-based reagents which, however, require harsh reaction conditions, long reaction times and/or the use of HMPT as a toxic additive, see: (a) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1982, 47, 1831.
  • 89
    • 49749092857 scopus 로고    scopus 로고
    • For the use of microwave irradiation in the cleavage or trans protection of aryl methyl ether using different reagents, see:
    • For the use of microwave irradiation in the cleavage or trans protection of aryl methyl ether using different reagents, see:
  • 92
    • 49749132501 scopus 로고    scopus 로고
    • DMF (99.8, Fluka) was stored over molecular sieves. GC-MS measurements were carried out on an Agilent HP6890 instrument with MS detector 5937 N using an Optima 1 MS (Macherey-Nagel) 30 m x 0.25 mm capillary column with H 2 as carrier gas. NMR data were measured on Bruker DPX 300 and AC 250 instruments. Chemical shifts (δ) are given in ppm relative to the solvent reference as the internal standard. Reactions under microwave irradiation were performed in a CEM Discover instrument (300 W) in glass tubes with temperature and pressure control. Preparation of the Reagent (LiSEt, In a dry 500-mL Schlenk flask a solution of n-BuLi (1.3 M) in hexane (120 mL, 160 mmol) was diluted with hexane (150 mL) under an argon atmosphere. The solution was cooled to 0 °C and under rapid stirring EtSH (200 mmol, 1.25 equiv, 15 mL) was added dropwise, whereupon a white precipitate formed. The reaction mixture was stirred at 0 °C for 10 min and at r.t. for 30 min. After
    • +, 219 (95), 217 (97), 191 (46), 189 (55), 173 (29), 171 (31), 110 (14), 67 (41).


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