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

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.