The Darzens glycidic ester condensation of indan-1-ones. A reinvestigation of the reaction

Abstract

The Darzens glycidic ester condensation of indan-1-one (1a) with ethyl chloroacetate was reinvestigated. Contrary to previous reports, the reaction proceeded normally yielding the glycidic ester 2a in high yield. Similarly, 5-cyclohexylindan-1-one (1b) produced the glycidic ester 2b. The glycidic esters 2a,b were converted to the corresponding aldehydes 4a,b by hydrolysis and decarboxylation. Oxidation of 4b yielded (±)-5-cyclohexylindan-1-carboxylic acid (3), a potent anti-inflammatory agent.