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Report | Regular issue | Vol 23, No. 3, 1985, pp.585-592
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0585
Lithiation Reactions of 5-Alkoxymethyl-, 5-Alkylthiomethyl-, and 5-Dialkylaminomethylisoxazoles

Ronald G. Micetich,* Chia C. Shaw. Tse W. Hall, Paul Spevak, and Buljit K. Bains

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


The 5-alkoxymethyl- and 5-alkylthiomethylisoxazoles undergo exclusive lateral lithiation at the C-5 methylene, the products reacting separately with methyl iodide, dimethyl disulfide, and carbon dioxide to give after work up the respective 5α-alkoxyethyl, 5α-alkylthioethyl , the mixed acetal, the thioacetal, the α-alkoxy acid and the α-thioalkoxy acid of the isoxazoles. This reaction can be repeated to give the mixed ortho ester, the thio ortho ester, the mixed α-ketal acid, and the mixed-thioketal acid. This method provides a very convenient route to these classes of compounds. The 5-dialkylaminomethylisoxazole is lithiated at the C-4 position.