Methyl iodide → (4S)-4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydronaphthalen-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-one (1) (2.0 g, 6.89 mmol) in THF (50 mL) at −78° C. was added LiHMDS (1.0 M in THF, 8.27 mL, 8.27 mmol). The reaction mixture was stirred for 20 min at −78° C. before MeI (1.17 g, 0.52 mL, 8.27 mmol) was added. The reaction mixture was stirred and warmed to 0° C. over 2 h before being quenched by a saturated solution of NH4Cl (20 mL). The product was extracted with ethyl acetate (100 mL ×2), dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:7 to 1:5) to give (S)-4-(3,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (56) (0.33 g, 15%) and (4S)-4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydronaphthalen-1 (2H)-one (55) (1.25 g, 60%).

Provenance & Evidence