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Synlett
Volumn , Issue 12, 2008, Pages 1789-1792
One-pot oxidative conjugate hydrothiocyanation-hydrosulfenylation of Baylis-Hillman alcohols promoted by a protic ionic liquid
Author keywords

Baylis Hillman alcohols; Conjugate addition; Methyl cinnamates; Oxidation; Protic ionic liquids; Stereoselective synthesis
Indexed keywords

ALCOHOL; CINNAMIC ACID DERIVATIVE; IONIC LIQUID; METHYL BETA THIOCYANATO ALPHA FORMYLHYDROCINNAMATE DERIVATIVE; METHYL(E) ALPHA FORMYLCINNAMATE DERIVATIVE;
EID: 48349124698     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078549     Document Type: Article
Times cited : (26)
References (82)
  • 1
    • 48349085728 scopus 로고    scopus 로고
    • Baylis, A. B.; Hillman, M. E. D. Offenlegungsschrift 2155113, 1972; US 3,743,669, 1972; Chem. Abstr. 1972, 77, 34174.
    • (a) Baylis, A. B.; Hillman, M. E. D. Offenlegungsschrift 2155113, 1972; US 3,743,669, 1972; Chem. Abstr. 1972, 77, 34174.
  • 2
    • 0000892247 scopus 로고    scopus 로고
    • Wiley: New York
    • (b) Ciganek, E. In Organic Reactions, Vol. 51; Wiley: New York, 1997, 201.
    • (1997) Organic Reactions , vol.51 , pp. 201
    • Ciganek, E.1
  • 54
    • 0037140770 scopus 로고    scopus 로고
    • ( 14) (a) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. Jr. J. Am. Chem. Soc. 2002, 124, 5962.
    • ( 14) (a) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. Jr. J. Am. Chem. Soc. 2002, 124, 5962.
  • 55
  • 67
    • 48349097068 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Methyl β-Thiocyanato- α-formylhydrocinnamates 3 and Methyl β-Phenylsulfenyl-α- formylhydrocinnamates 4 A mixture of BH alcohol 1 (1 mmol) and NaNO3 (1 mmol) was stirred in 1 mL of [Hmim]HSO4 at 80°C for 1-3 h (Table 2, The reaction mixture was cooled to r.t. and NH4SCN or PhSH (1.1 mmol) was added. The mixture was further stirred at r.t. for 2-3 h. After completion of the reaction (monitored by TLC, the product was extracted with EtOAc (3 x 10 mL, The combined extract was dried over MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane-EtOAc, 8.5:1.5) to afford the desired product 3 or 4. After isolation of the product, the remaining ionic liquid was washed with Et2O (2 x 10 mL) to remove any organic impurity, then H2SO4 2.1 mmol in the case of compound 3
    • 5S: C, 59.12; H, 4.38; N, 4.06. Found: C, 59.33; H, 4.74; N, 3.89.
  • 79
    • 48349137577 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Methyl (E, α-Formylcinnamates 2 A stirred solution of BH alcohols 1 (1 mmol) and NaNO3 (1 mmol) in 1 mL of [Hmim]HSO4 was heated at 80°C for 1-3 h (Table 2, The reaction progress was monitored by TLC Upon completion, the reaction mixture was cooled to r.t. and extracted with EtOAc (3 x 10 mL).The combined organic phase was dried over MgSO4, filtered, and evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a gradient mixture of hexane-EtOAc (8:2) as eluent to give the pure cinnamates 2. The remaining ionic liquid was recycled for subsequent runs as described above using H2SO 4 (1 mmol).16 Data of Representative Compound Compound 2a: white solid, yield 80, mp 91-92°C IR KBr, 3076, 2809, 2740, 1724, 1684, 1578, 1462, 1286, 1190, 760, 712 cm-1
    • 3: C, 69.46; H, 5.30. Found: C, 69.81; H, 5.14.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.