C(OCC)(=O)C.C(=O)([O-])O.[K+].[CH:12]#[C:13][CH:14]([OH:17])[CH2:15][CH3:16].[Br:18][C:19](Br)=[N:20][OH:21]>O>[Br:18][C:19]1[CH:12]=[C:13]([CH:14]([OH:17])[CH2:15][CH3:16])[O:21][N:20]=1Added 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. 102° C/2 mmHg.
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