Potassium Hydroxide → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-

Participants

Reaction Steps

In a 100 ml. round bottom 3-neck flask there was placed 2 g. of pivalyl acetonitrile, 0.9 g. of potassium hydroxide, 25 ml. of ethanol, and 35 ml. of water. The mixture was heated to refluxing, and an aqueous solution of hydroxylamine hydrochloride was added. After the addition was complete, the mixture showed a pH of 5.6. The pH was immediately adjusted to 6.2 by adding aqueous saturated sodium bicarbonate solution. The pH of the reaction mixture after 1 hour was 6.3. After 2 hours, the pH of the reaction mixture was 6.4. After 3 hours, the pH of the reaction mixture was 6.5. The reaction mixture was allowed to reflux overnight, and the following morning the pH was 6.8. The reaction mixture was cooled and the ethanol stripped on the rotovapor. The white solid which separated was filtered off and dried. The solid weighed 0.8 g., and was determined by vpc to contain 91.9% 3-amino-5-(t-butyl)isoxazole and 5.7% of 5-amino-3-(t-butyl)isoxazole. Yield of desired isomer was 48%.

Provenance & Evidence