Cyclohexanone → 2-(3-Methoxyphenyl)cyclohexanone

Participants

Reaction Steps

To 1.6 M n-BuLi in hexane (12.5 mL, 20 mmol) at 0° C. was added a solution of 2,2,6,6-tetramethyl piperidine (3.4 mL, 20 mmol) in anhydrous THF (40 mL) over 5 min. Cyclohexanone (2.1 mL, 20 mmol) was added dropwise. After stirring the reaction mixture for 10 min, a further portion of 1.6M n-BuLi in hexane (12.5 mL, 20 mmol) was added, the mixture stirred for 10 min, and 2-chloroanisole (2.5 mL, 20 mmol) was added. After stirring for 30 min under Ar, the reaction mixture was quenched with H2O (300 mL) and extracted with EtOAc (150 mL). The organic layer was separated, washed with 2N HCl (100 mL), H2O (200 mL) and brine, then dried (MgSO4). Filtration and concentration gave the title compound after SiO2 chromatography (CHCl3:MeOH, 200:1).

Provenance & Evidence