Acetone → HCID 11501747, compound

Participants

Reaction Steps

To a solution of 1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-5-(methylsulfonyl)-1H-benzimidazole (Step D, 8.22 g, 25.7 mmol) in tetrahydrofuran (200 mL) was added lithium bis(trimethylsilyl)amide (1.07 M in hexane, 28.8 mL, 30.8 mmol) at −40° C. under nitrogen atmosphere. After stirring for 10 min, acetone (20 mL) was added at −40° C. and the mixture was allowed to warm to room temperature. After stirring for 18 h, the mixture was quenched with water (200 mL) and extracted with ethyl acetate (300 mL×3). The combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2 as eluent) to afford the title compound (4.68 g, 48%) as a white solid.

Provenance & Evidence