Acetic Acid → 7-(1-Ethylpropyl)-2-(mesitylmethyl)-1-methyl-1H-benzimidazole

Participants

Reaction Steps

To a solution of 7-[1-ethylprop-1-en-1-yl]-2-(mesitylmethyl)-1-methyl-1H-benzimidazole (110 mg, 0.331 mmol) in tetrahydrofuran (3.5 mL) was added a solution of borane-dimethyl sulfide complex in tetrahydrofuran (1.9 M, 3.5 mL, 6.63 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 15 hr, acetic acid (5.0 mL) was added to the mixture and the mixture was heated at 120° C. for 2 hr. After the reaction mixture was cooled, the mixture was poured into saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (50 mL, twice). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 10-25% ethyl acetate/n-hexane gradient mixture to give the title compound (12 mg, 0.0359 mmol, 11%) as a colorless solid.

Provenance & Evidence