Cyclohexanone, 4,4-dimethyl- → 4-Methoxymethylene-1,1-dimethyl-cyclohexane

Participants

Reaction Conditions

Reaction Steps

n-BuLi (2.6 M in hexane, 2.3 mL, 5.94 mmol) was added dropwisely to a stirred solution of (methoxymethyl)triphenylphosphonium chloride (2.04 g, 5.94 mmol) in THF (20 mL) at −78° C. and stirred for 10 min at the same temperature and then stirred for 2.5 h at room temperature. The reaction mixture was cooled down to −78° C., a solution of 4,4-dimethylcyclohexanone (500 mg, 3.96 mmol) in THF (5 mL) was added slowly at −78° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for overnight. The reaction mixture was quenched with sat. NaHCO3 aq. (20 mL) and extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure to provide compound A12-1 (512.2 mg, crude) as pale yellow oil. The crude product was used for next step without purification.

Provenance & Evidence