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Synthesis 2012(2): 283-289  
DOI: 10.1055/s-0031-1289647
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Akula Raghunadha, Suresh Babu Meruvaa, Nuka Anil Kumara, Gudla Santosh Kumara, L. Vaikunta Raob, 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
Further Information

Publication History

Received 14 July 2011
Publication Date:
16 December 2011 (online)

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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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