Ethyl Acetate → 3-Bromo-5-(1-hydroxypropyl)isoxazole

Participants

Reaction Steps

Added to 800 ml of ethyl acetate were 8 ml of water, 60.0 g (0.6 mol) of potassium hydrogencarbonate and 73.5 g (0.88 mol) of 1-pentyn-3-ol. Under stirring, 40.5 g (0.2 mol) of dibromoformaldoxime were added at room temperature over 3 hours. After the resultant mixture was stirred at room temperature for 16 hours, water was added and the reaction product was extracted with ethyl acetate. Subsequent to concentration, 3-bromo-5-(1-hydroxypropyl) isoxazole was obtained as oil. It was distilled to collect a fraction at 97°-102° C./2 mmHg. Analytical results of the fraction obtained: Yield: 18 g (74%).

Provenance & Evidence