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Synthesis 2006(11): 1763-1766  
DOI: 10.1055/s-2006-942351
PAPER
© Georg Thieme Verlag Stuttgart · New York

Preparation of 2-(1-Chloroalkyl)-4,5-dimethyloxazoles and (E)-2-Alkenyl-4,5-dimethyloxazoles

Hua Zhanga-c, Peng-Fei Yanc, Guo-Lin Zhang*a
a Chengdu Institute of Biology, The Chinese Academy of Sciences, Chengdu 610041, P. R. of China
Fax: +86(28)85225401; e-Mail: zhanggl@cib.ac.cn;
b Graduate School of the Chinese Academy of Sciences, Beijing 100039, P. R. of China
c College of Chemical Engineering and Material of Heilongjiang University, Haerbin 150080, P. R. of China
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Publication History

Received 9 November 2005
Publication Date:
05 May 2006 (online)

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Abstract

2-(1-Chloroalkyl)-4,5-dimethyloxazoles were prepared in 84-91% yields by simultaneous reduction and regioselective chlorination of the corresponding unstable N-oxides with POCl3 or SOCl2. Dehydrochlorination of 2-(1-chloroalkyl)-4,5-dimethyloxazoles with potassium hydroxide afforded (E)-2-alkenyl-4,5-di­methyloxazoles in 71-90% yields.

Key words

oxazole - chlorination - regioselectivity - dehydrochlorination