Studies on the reaction of organotin phenoxides with ethyl propiolate catalysed by triethylamine and tin(IV) chloride

Abstract

Different tributyltin phenoxides react at room temperature with ethyl propiolate in benzene, in the presence of tin(IV) chloride, triethylamine and their mixture to give the derivatives of 3-phenoxyacrylic acid ethyl ester. Exceptionally, 3-(2-hydroxyphenyl)acrylic acid ethyl ester and 3-(2-hydroxy-5-methylphenyl)acrylic acid ethyl ester have been obtained from the reaction of tributylphenoxytin and tributyl(p-tolyloxy)tin, respectively catalysed by SnCl 4 , and they have been easily hydrolysed to coumarin and 6-methylcoumarin.