Deconjugative Esterification of &alpha,&beta-Unsaturated Carboxylic Acids through Carbodiimide Coupling

DOI
  • Ichikawa Takashi
    Graduate School of Pharmaceutical Sciences, The University of Tokushima
  • Nakao Michiyasu
    Graduate School of Pharmaceutical Sciences, The University of Tokushima
  • Sano Shigeki
    Graduate School of Pharmaceutical Sciences, The University of Tokushima
  • Nagao Yoshimitsu
    Graduate School of Pharmaceutical Sciences, The University of Tokushima

Bibliographic Information

Other Title
  • カルボジイミド型脱水縮合剤を用いるα,β-不飽和カルボン酸の脱共役エステル化反応

Description

We have disclosed the deconjugative esterification of &alpha,&beta-unsaturated carboxylic acids through 1,3-dicyclohexylcarbodiimide (DCC) coupling. In the presence of trimethylamine hydrochloride and N,N-dimethylethylamine, an esterification of (E)-5-phenylpent-2-enoic acid and isopropanol through DCC coupling in CH2Cl2 at 50ºC afforded &beta,&gamma-unsaturated ester as a major product with a ratio of 91:9. The tendency toward deconjugation in the esterification seemed to depend on the bulkiness of alcohols. The reaction probably involves the generation of a conjugated ketene intermediate, which is converted into the corresponding &beta,&gamma-unsaturated esters by treatment with alcohols.

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Keywords

Details 詳細情報について

  • CRID
    1390001205635773568
  • NII Article ID
    130006998329
  • DOI
    10.14895/hannou.35.0.108.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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