GaCl3-promoted ethenylation of thioester silyl enolate and dienolate with silylethyne

Chemistry Letters

Volumn , Issue 11, 2001, Pages 1080-1081

  Arisawa, Mieko ^a   Miyagawa, Chie ^a   Yoshimura, Satoru ^a   Kido, Yoshiyuki ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035541145     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.1080     Document Type: Article

References (14)

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4. 3 (1.0 M, 2.0 mmol) in methylcyclohexane (2.0 mL) was added to a mixture of S-ethyl 3-phenylpropanethioate silyl enol ether (0.5 mmol, 133 mg) and trimethylsilylethyne (0.14 mL, 1.0 mmol) in methylcyclohexane (2.0 mL) at room temperature. After being stirred at room temperature for 5 min, THF (5.0 mL) was added to dissolve the insoluble materials. Sulfuric acid (6 M, 5.0 mL) was added, and stirring was continued for another 5 min. Then, the organic materials were extracted twice with ether. The combined organic layers were washed with water and brine, dried over magnesium sulfate, and concentrated. The residue was purified by flash column chromatography to give S-ethyl 2-ethenyl-3-phenylpropanethioate (93.5 mg, 85%).
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