J. Rouchaud, F. Gustin, Claude Moulard
Sep 1, 2010
Citations
0
Influential Citations
3
Citations
Journal
Bulletin des Sociétés Chimiques Belges
Abstract
Methyl 2-ethylbutyrate (3) plus lithiumdiisopropylamide reacted with methyl iodide to give methyl 2-ethyl-2-methylbutyrate (4). The methylene carbanion of acetonitrile -generated with lithiumdiisopropylamide- reacted with 4 to give 4-ethyl-4-methyl-3-oxohexanenitrile (5). 3-Ketonitrile 5 reacted with hydroxylamine after 20 min of heating to reflux in ethanol to give 4-ethyl-4-methyl-3-oxohexanitrile oxime (6). This in aqueous dilute HCl was selectively and quantitatively transformed into 5-amino-3 (1-ethyl-1-methylpropyl)isoxazol (7). Longer heating of 5 with hydroxylamine directly generated a mixture of 7 with its isomer 3-amino-5-(1-ethyl-1-methylpropyl)isoxazol (7b). Reaction conditions were studied for optimization of the 5-aminoisoxazol 7 synthesis.