Cyclohexanone, 2-[(phenylmethoxy)methyl]- → (((2-Methylenecyclohexyl)methoxy)methyl)benzene

Participants

Reaction Conditions

Reaction Steps

An oven-dried 250 mL one-necked round bottomed flask was charged with methyltriphenylphosphonium bromide (4.3 g, 12.3 mmol) and dry THF (20 mL) and then cooled to −78° C. To this solution was added n-BuLi (2.8 M in hexane, 4.3 mL, 12.3 mmol) over 10 min by syringe. The resultant red ylide solution was then warmed to rt, stirred for 3 hours, and cooled to −78° C. To this ylide solution was added 2-((benzyloxy)methyl)cyclohexanone (1.8 g, 8.6 mmol) in dry THF (5 mL) via syringe over 10 min. After being stirred for 1 hour at −78° C., the reaction mixture was warmed to rt slowly and stirred for 10 hours. After that the reaction mixture was cooled to 0° C., quenched with aq. NaHCO3 (60 mL), and extracted with ether (3×60 mL). The organic layer was washed with brine (60 mL) and dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed with hexane-Et2O isocratic 10% as eluant to give the title compound as clear oil. MS m/z 217.1 (M+1).

Provenance & Evidence