反应详情

温度

25 °C

A solution of 2-pentadecynenitrile (10.0 g, 45.6 mmol) in ethanol (50 mL) was added to a stirred solution of hydroxylamine hydrochloride (3.8 g, 54.6 mmol) in 2.5 N NaOH (20.0 mL, 50.1 mmol). The resulting mixture was diluted with ethanol (100 mL) and stirred (22 hours, 25° C.). The obtained slurry was concentrated, then partitioned between ethyl acetate (300 mL) and brine (100 mL). The organic layer was dried (MgSO4), concentrated in vacuo, and chromatographed on silica (95:5 to 70:30 hexane:ethyl acetate) to yield 8.2 g (71.2%) of 5-amino-3-dodecyl-isoxazole as a waxy solid, m.p. 48.5°-49.5° C.

1. concentrationThe obtained slurry was concentrated
2. custompartitioned between ethyl acetate (300 mL) and brine (100 mL)
3. dry with materialThe organic layer was dried (MgSO4)
4. concentrationconcentrated in vacuo
5. customchromatographed on silica (95:5 to 70:30 hexane:ethyl acetate)