A New Entry to 1,5-Keto Esters and Their 4,4-Dideuterio Derivatives via Methylene Chloride as “Methylene Dianion” Equivalents

Kuo-Wei Lin, Cheng-Yih Chen, Wei-Fan Chen and Tu-Hsin Yan*

*Department of Chemistry, National Chung-Hsing University, Taichung 400, Taiwan, Republic of China, Email: thyanmail.nchu.edu.tw

K.-W. Lin, C. Y. Chen, W.-F. Chen, T.-H. Yan, J. Org. Chem., 2008, 73, 4759-4761.

DOI: 10.1021/jo800732s

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Abstract

A TiCl₄-Mg promoted coupling of various amides with CH₂Cl₂ and methyl acrylate allows an extremely simple and practical synthesis of 1,5-keto esters. The efficiency of this chemistry is illustrated by the very simple preparation of unusual 4,4-dideuterio-1,5-keto esters using CD₂Cl₂.

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Key Words

Carbonyl Compounds, Esters

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ID: J42-Y2008-1680