Diisobutylaluminumhydride → HCID 14849865, compound

Participants

Reaction Steps

Methyl (E)-3-[5-(4-fluorophenyl)-2-(1-methylethyl)-4-(3-pyridinyl)-1H-imidazol-1-yl]-2-propenoate, 1'-oxide (0.18 g) in dichloromethane (3 ml) at 3° under nitrogen was treated with diisobutylaluminium hydride (1.5M in toluene; 0.94 ml). The mixture was stirred at 0° for 1 h and then quenched with water (1 ml) and extracted with ethyl acetate. The extracts were washed with brine, dried and evaporated. The residue was purified by CC eluting with a mixture of ethyl acetate, petroleum ether (bp. 40°-60°) and methanol (10:10:3) to give the title compound (0.05 g), δ(CDCl3) 8.60(m,1H,C-2 proton of pyridine), 8.48(m,1H,C-6 proton of pyridine), 7.81(m,1H, C-3 proton of pyridine), 6.63(d,1H,J15 Hz,NCH=CH), 5.56(dd,1H, J15 and 6 Hz,NCH=CH), 4.18(m,2H,CH2OH), 3.17(septet,1H,J7 Hz, CH(CH3)2), 1.42(d,6H,J7 Hz,CH(CH3)2).

Provenance & Evidence