Natural benzofurans. Synthesis of medicagol methoxybenzofuran

A general route to 2-arylbenzofurans, consisting of reaction of an o-halogenophenol ester with a cuprous arylacetylide, was employed to synthesize medicagol methoxybenzofuran. 2,4-Diraethoxyacetophenone was converted to 2,4-dimethoxyphenylacetylene in three steps and reaction of the cuprous salt with 2-iodo-4,5-methylenedioxyphenyl acetate gave the desired 2-(2′,4′-dimethoxyphenyl)-5,6-methylenedioxybenzofuran.