3-(Furyl)-3-(diethoxyphosphoryl)acrylates: Synthesis and reaction with nitromethane

Abstract

A series of 3-(furyl)-3-(diethoxyphosphoryl)acrylates was synthesized by the reaction of 2- and 3-furoyl phosphonates with ethoxycarbonylmethylenetriphenylphosphorane. It was shown that in all cases diethoxyphosphoryl and ester groups were in trans-position with respect to the double bond disregarding the structure of the furan fragment. Potassium fluoride catalyzed addition of nitromethane to the compounds synthesized was studied. It was found that this reaction proceeded regioselectively to form 2-[(furyl)(diethoxyphosphoryl) methyl]-3-nitropropanoic acids.