A Malonic Ester Synthesis with Acid Chlorides. The Homologation of Oioic Acids

Abstract

Abstract Recently we reported1 that sodium cyanoborohydride in acetic acidis an effective reagent for the reduction of acylated derivatives of barbituric acid, Meldrum's acid, and 4-hydroxy-coumarin to the corresponding alkyl derivatives. Since Meldrum's acid can be readily acylated2, and since the alkyl derivatives can be readily hydrolyzed and decarboxylated to alkanoic acids3, this reductive transformation would complete a synthetic method similar to the malonic ester synthesis except that acid chlorides could be employed in place of alkyl halides.