Ammonium formate → HCID 58653653, compound

Participants

Reaction Steps

To a solution of ethyl 3-(1H-benzimidazol-1-yl)-3-(4-ethylphenyl)-2-propenoate (E/Z mixture, 181 mg, 566 μmol) in a mixture of ethanol and water (10:1, 2.75 mL) was added palladium on carbon (27 mg, 10% w/w Pd) and ammonium formate (143 mg, 2.26 mmol). The suspension was brought to reflux for 3 hours, cooled to room temperature, and was filtered through a pad of Celite® and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (96:4) to afford the title compound, 1H NMR: (CDCl3), 8.03 (s, 1H), (d, J=6.96, 1H), 7.31-7.06 (m, 7H), 6.01 (dd, J=8.79, 6.59, 1H), 4.04 (t, J=6.96, 2H), 3.38 (dd, J=15.75, 8.79, 1H), 3.31 (dd, J=15.75, 6.59, 1H), 2.62 (q, J=7.69, 2H), 1.18 (t, J=7.69, 3H), 1.09 (t, J=6.96, 3H).

Provenance & Evidence