The reduction of 3-substituted furans with lithium and ammonia

Abstract

The reductions of 3-(1',1'-ethylenedioxynonyl)furan, 3-(1',1'-dimethoxynonyl)furan, 3-(1'-methoxynonyl)furan and 1-(furan-3'-yl)nonyl acetate with lithium and ammonia are described. The products result from benzylic type cleavage in the absence of an added proton source. When ethanol is present during the reduction extensive saturation and fission of the furan ring occurs.