Benzyl Bromide → HCID 86747873, compound

Participants

Reaction Steps

A solution of ethyl (E)-4-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-3-butenoate (256 mg, 0.709 mmol) in tetrahydrofuran (5 mL) was cooled to -78° C. under argon, and lithium diisopropylamide (0.85 mmol, 1 M in tetrahydrofuran) was added. After 10 minutes benzyl bromide (243 mg, 1.42 mmol) was added. The mixture was then stirred at room temperature overnight, diluted with 10% ammonium chloride and extracted with ethyl acetate. The dried, concentrated product was chromatographed over silica gel with 6:4 hexane/ethyl acetate to give 128 mg (33%) of the title compound as an oil. NMR indicated the bis(benzyl) substitution.

Provenance & Evidence