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

Hua Zhang; Peng-Fei Yan; Guo-Lin Zhang

doi:10.1055/s-2006-942351

PAPER

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

Hua Zhang^a-c, Peng-Fei Yan^c, 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

Abstract

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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

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References

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