Synthesis of methyl 2-Oxotetralin-1-carboxylates

Abstract

The base-catalysed reaction of dimethyl carbonate with 2-tetralones has been found to lead to the formation of methyl 2-oxotetralin-1-carboxylates (1). This constitutes an excellent method of synthesis of the title compounds. Thus the tetralone (2b) on reaction with dimethyl carbonate and sodium hydride gave the keto ester (lb) in 92% yield. The extent of enolization of these tetralone esters was found to depend on the size of the substituent in the C8 position.