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Report | Regular issue | Vol 23, No. 3, 1985, pp.571-583
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0571
The 5-Alkoxymethyl-, 5-Alkylthiomethyl-, and 5-Dialkylaminomethylisoxazoles

Ronald G. Micetich,* Chia C. Shaw, Tse W. Hall, Paul Spevak, Robert A. Fortier, Peter Wolfert, Brian C. Foster, and Buljit K. Bains

*Faculty of Pharmacy , University of Alberta, Edmonton, Alberta T6G, 2N8, Canada

Abstract

A variety of methods were used for the preparation of the 5-alkoxymethyl-, 5-alkylthiomethyl-, and 5-dialkylaminomethylisoxazoles. A novel method for the separation of the isomeric mixture of 3-(5-)methoxymethyl-5-(3-)methylisoxazoles (obtained by reaction of 1-methoxypentane-1,3-dione with hydroxylamine), based on the difference in reactivity with n-butyllithium, is described. Methods for the preparation of 5-alkylthimethylisoxazoles from the 5-methylisoxazoles; and 5-alkoxymethylisoxazoles from the 5-hydroxymethylisoxazoles are also reported.