Deng Yong
2010
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Journal
West China Journal of Pharmaceutical Sciences
Abstract
OBJECTIVE To investigate a practical and convenient process for the synthesis of 3-(2,3-dihydrobenzofuran-5-yl) propanoic acid.METHODS 3-(2,3-Dihydrobenzofuran-5-yl) propanoic acid was synthesized by methyl esterification of 3-(4-hydroxyphenyl) acrylic acid,followed by condensation with bromoacetaldehyde diethyl acetal and Friedel-Crafts reaction to give methyl 3-(benzofuran-5-yl) acrylic acid,which was subsequently subjected to catalytic hydrogenation in the presence of 10% Pd/C and hydrolysis to afford 3-(2,3-dihydrobenzofuran-5-yl) propanoic acid.RESULTS The chemical structure of 3-(2,3-dihydrobenzofuran-5-yl) propanoic acid was determined by ~1HNMR and ESI-MS.The overall yield was 60%.CONCLUSION This process,as compared to the previously reported methods,has advantages of milder reaction condition,simpler operation and high yield.