Hexane → HCID 19006051, compound

Participants

Reaction Steps

A stirred solution of 2.5M n-butyllithium in hexane (30.8ml, 0.77mol) at -78° C. was mixed with diethyl ether (310ml) and a solution of 4-bromopyridine (60.9g, 0.39mol) in diethyl ether (1200 ml) was added dropwise over 3 hours. Stirring was continued for 2 hours and a solution of 2-methoxycyclohexanone (54.3g, 0.42mol) in diethyl ether (total volume 100ml) was added dropwise over 1 hour. The stirred solution was allowed to warm to room temperature and stirring was continued overnight. Water (250ml) was then added to the reaction mixture, keeping the temperature below 20° C. and the mixture stirred for a further 30 minutes. The organic layer was separated and the aqueous layer was extracted with diethyl ether (3×50ml). The combined organic layers were extracted with hydrochloric acid (2N, 2×250ml+100ml) and the combined acidic extracts brought to pH 11 with 5N aqueous sodium hydroxide and extracted with ethyl acetate (3×250ml). The combined ethyl acetate extracts were dried (MgSO4) and evaporated in vacuo. The residue was recrystallized from petroleum ether (60°-80° C.) to give (±)-2-methoxy-l-(pyrid-4-yl)cyclohexanol (32.0g, 0.15mol) as a mixture of cis and trans isomers, m.p. 98°-101° C.

Provenance & Evidence