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Swern Oxidation of Alcohols with Ion-Supported Methyl Sulfoxide and Oxalyl Chloride

Daisuke Tsuchiya, Katsuhiko Moriyama, Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: togofaculty.chiba-u.jp

D. Tsuchiya, K. Moriyama, H. Togo, Synlett, 2011, 2701-2704.

DOI: 10.1055/s-0031-1289552 (free Supporting Information)


Abstract

The oxidation of primary and secondary alcohols with ion-supported methyl sulfoxide and oxalyl chloride in the presence of triethylamine in dichloromethane efficiently gives carbonyl compunds in good yields with high purity. Isolation of the product was achieved very easily by simple diethyl ether extraction of the reaction mixture. Furthermore, ion-supported methyl sulfide was recovered in good yield and re-oxidized.

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Key Words

Swern oxidation, ion-supported methyl sulfoxide, alcohols, aldehydes, ketones, reuse


ID: J60-Y2011-3260