96603-47-3Relevant academic research and scientific papers
LITHIATION REACTIONS OF 5-ALKOXYMETHYL-, 5-ALKYLTHIOMETHYL-, AND 5-DIALKYLAMINOMETHYLISOXAZOLES
Micetich, Ronald G.,Shaw, Chia C.,Hall, Tse W.,Spevak, Paul,Bains, Buljit K.
, p. 585 - 592 (2007/10/02)
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-thioalkoxyacid 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.
