Practical and convenient synthesis of coumarins from phenols and propiolic acid esters.
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.
Kitamura
Tsugio
T
Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan.
Oyamada
Juzo
J
Tsubota
Toshiyuki
T
D000480:Alkynes / Q000737:chemistry*; D052117:Benzodioxoles / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D004149:Dioxoles / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*
C520566:6,7-methylenedioxy-4-phenylcoumarin; D000480:Alkynes; D052117:Benzodioxoles; D003374:Coumarins; D004149:Dioxoles; D010636:Phenols; C015202:ethylphenylpropiolate; C025583:sesamol