An Efficient and Practical Synthesis
of Aryl and Hetaryl α-Keto Esters

Akula Raghunadh; Suresh Babu Meruva; Nuka Anil Kumar; Gudla Santosh Kumar; L. Vaikunta Rao; U. K. Syam Kumar

doi:10.1055/s-0031-1289647

PAPER

An Efficient and Practical Synthesis of Aryl and Hetaryl α-Keto Esters

Akula Raghunadh^a, Suresh Babu Meruva^a, Nuka Anil Kumar^a, Gudla Santosh Kumar^a, L. Vaikunta Rao^b, U. K. Syam Kumar*^a
^a Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd., Miyapur, Hyderabad, 500 049, India
Fax: +91(40)23045439; e-Mail: syam_kmr@yahoo.com;
^b Gitam University, Gandhi Nagar, Rushikonda, Visakhapatanam 530 045, India

Abstract

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Abstract

A general and highly efficient method was developed for the synthesis of α-keto esters by oxidative esterification of 2,2-dibromo-1-(het)arylethanones by sequential treatment with dimethyl sulfoxide and an alkanol. The versatility of the reaction was established by synthesizing a range of α-keto esters by treatment of 2,2-dibromoethanones, derived from aryl or hetaryl ketones, with dimethyl sulfoxide and a cyclic or acyclic primary or secondary alcohol. The mechanism of the reaction was established by means of a detailed study.

Key words

ketones - esters - oxidations - esterifications - alcohols

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