Methanol → HCID 13645760, compound

Participants

Reaction Steps

The 2-phenyl-1-(2-propenyl)-cyclohexanecarboxylic acid ethyl ester (4.08 g, 15 mmol) was dissolved in THF (10 ml) and cooled to 0°, under nitrogen. Upon addition of 5.2 ml of 1M BH3 -THF, the solution was stirred at 0° for 30 min. then at RT for 30 min. The flask was cooled to 0° and 0.5 ml MeOH was added to destroy any excess hydride. Bromine (1 ml, 20 mmol) was added dropwise followed by the addition of 30 mmol of freshly prepared NaOMe (0.7 g Na metal/10 ml anhydrous MeOH). The color of the solution changes from bright yellow to clear. Stirring was continued for 30 min. Water (50 ml) was added and the solution was extracted with Et2O (2×50 ml). The combined organic extracts were washed with brine and dried over MgSO4. Filtration and concentration in vacuo of the organic material afforded 5.44 g crude. Distillation yielded 4.38 g (83%) of 1-(3-bromopropyl)-2-phenylcyclohexanecarboxylic acid ethyl ester as a yellow viscous oil.

Provenance & Evidence