par Rouchaud, Jean;Gustin, Fabrice;Moulard, Claude
Référence Bulletin des Sociétés chimiques belges, 102, 8, page (545-555)
Publication Publié, 1993
Article révisé par les pairs
Résumé : 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 HC1 was selectively and quantitatively transformed into 5‐amino‐3‐(l‐ethyl‐l‐methylpropyl)‐isoxazol (I). Longer heating of 5 with hydroxylamine directly generated a mixture of 7 with its isomer 3‐amino‐5‐(l‐ethyl‐l‐methylpropyl)isoxazol (7b). Reaction conditions were studied for optimization of the 5‐aminoisoxazol 7 synthesis. Copyright © 1993 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim