Cerium(III) chloride → HCID 59140412, compound

Participants

Reaction Steps

Cerium Chloride (1.625 g, 6.59 mmol) was added to an ambient temperature solution of 2-[(4-bromophenyl)acetyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (Intermediate 8) (1 g, 2.2 mmol) in tetrahydrofuran (22 mL). After stirring at ambient temperature for 1 h, the reaction mixture was cooled to 0° C. and methylmagnesium bromide (3 M in diethyl ether) (2.2 mL, 6.59 mmol) was added. After stirring at 0° C. for a further 30 min, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 2-[2-(4-bromophenyl)-1-hydroxy-1-methylethyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Provenance & Evidence