The reduction of 2-substituted furan derivatives with lithium and ammonia

Abstract

The reduction of 1-(furan-2'-yl)nonan-1-one with lithium and ammonia in the presence of alcohols gave 1-(2',3'-dihydrofuran-2'-yl)nonan-1-one as the major product or a mixture of 1-(tetrahydrofuran-2'-yl)nonan-1-one and tridecane-1,5-diol depending on the conditions. 1-(Furan-2'-y1)nonyl acetate, 2-(1'-methoxynonyl)furan, 1-(furan-2'-yl)nonan-1-ol, 2-(1',1'-ethylenedioxynonyl)furan and 2-(pent-1'-eny')furan have also been reduced both in the presence and absence of an alcohol.