Tetrahydrofuran → 22625-86-1

To 90 ml of dry tetrahydrofuran maintained in an inert atmosphere at -60° C. was added 45.3 ml of a 3.0M solution of methylmagnesium bromide in diethyl ether followed by dropwise addition of 15.6 g of 5-acetyl-1-methylcyclohexene in a solution of 50 ml dry tetrahydrofuran. The reaction mixture was warmed to -20° C. and stirred for two hours. The resulting reaction mixture was poured into 150 ml of chilled, saturated ammonium chloride solution and extracted three times with 300 ml portions of diethyl ether. The combined extracts were washed successively with 300 ml of water and 300 ml of saturated sodium chloride, dried (MgSO4) and concentrated in vacuo to leave 17.1 g of a pale yellow oil. Distillation of the oil gave 10.7 g of the desired product as a colorless oil, b.p. 63°-65° C. (0.65 mm).