Hexane → (+)-2-Methoxy-1-(pyrid-3-yl)cyclohexanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.5M n-butyl lithium in hexane (13.2 ml, 33 mmol) at -78° C. (was added diethyl ether (15 ml) followed by a solution of 3-bromopyridine (4.7 g, 30 mmol) in ether (90 ml) over a period of 10 minutes. After 1 hour at -78° C. a solution of (±)-2-methoxycyclohexanone (3.84 g, 30 mmol) in ether (20 ml) was added dropwise during 10 minutes. After 2 hours at -78° C. and 30 minutes at 0° C. the reaction mixture was warmed to 20° C. and then poured onto ice (150 g). The mixture was extracted with ether (2×50 ml) and then the combined organic extracts were extracted with 1N hydrochloric acid (50 ml). This aqueous extract was washed with ether (20 ml) and then treated with 2M sodium hydroxide solution (25 ml) and extracted with ether (3×100 ml). The organic extracts were combined, washed with brine then dried over anhydrous sodium sulphate. Concentration in vacuo afforded (±)-2-methoxy-1-(3-pyridyl)-cyclohexanol (5.0 g, 24 mmol) as a 4:1 mixture of cis and trans isomers; N.M.R. (CDCl3), 1.2-2.14 (c), 2.24-2.44 (m), 2.90-3.28 (c); 3.48-3.60 (m), 7.18-7.30 (m); 7.78-7.96 (m); 8.40-8.48 (m); 8.62-8.72 (m); 8.78-8.82 (m).

Provenance & Evidence