Dibutylamine → HCID 53779816, compound

Participants

Reaction Steps

A! A solution of 43 ml (0.25 mole) of dibutylamine in 770 ml of dichloromethane was added with a 0.91M solution of 280 ml (0.025 mole) of triethyl-aluminium in hexane, at 0° C. under argo, and the resultant reaction mixture was stirred for 30 minutes at room temperature, then dropwise added with 25.8 ml (0.25 mole) of 7-oxabicyclo[4.1.0]heptane, and stirred overnight. A 6M solution of 200 ml (1.2 moles) of sodium hydroxide was added very slowly, and the mixture was stirred for 2 hours at room temperature. The phases were separated, and the organic one was washed with water (2×50 ml), anhydrified over sodium sulfate and evaporated. The resultant crude was distilled under vacuum to provide 43.7 g (yield: 75%) of trans-2-(N,N-dibutylamino)-cyclohexanol (b.p.--105°-107° C./1 mmHg).

Provenance & Evidence