Sodium Hydroxide → 5-Amino-3-dodecylisoxazole

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence