Nature Protocols 2007-01-01

Practical and convenient synthesis of coumarins from phenols and propiolic acid esters.

Tsugio Kitamura, Juzo Oyamada, Toshiyuki Tsubota

Index: Nat. Protoc. 2(4) , 845-8, (2007)

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Abstract

This protocol describes the synthesis of 6,7-methylenedioxy-4-phenylcoumarin from sesamol and ethyl phenylpropiolate using a Pd(OAc)2 catalyst to illustrate coumarin synthesis. This procedure is simple and easy and can be applied to the synthesis of other coumarins that have electron-rich phenol groups. The reaction is conducted by stirring a solution of Pd(OAc)2, sesamol and ethyl phenylpropiolate in trifluoroacetic acid at room temperature (15-20 degrees C) under atmospheric conditions. This protocol can be completed in 3 d.