Diisobutylaluminumhydride → HCID 59240150, compound

Participants

Reaction Steps

To a −78° C. solution of ethyl 1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazole-4-carboxylate (1.00 g, 1.94 mmol) in 10 mL dichloromethane was added diisobutylaluminum hydride (9.7 mL, 9.70 mmol). The reaction was stirred from 78° C. to room temperature for 12 h. The reaction was quenched with 5 mL MeOH, followed by 10 mL Rochelle's salt. Dilute with ethyl acetate and stir for 1 h. The organic layer was separated and the water layer was extracted with ethyl acetate 1×10 mL. The combined organic layers were washed with brine and dried with MgSO4 to afford (1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazol-4-yl)methanol (770 mg, 84%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 8.21-8.20 (m, 1H), 8.10-8.07 (m, 1H), 8.05-8.04 (m, 1H), 7.95-7.92 (m, 1H), 7.80-7.77 (m, 1H), 7.74 (t, J=7.84 Hz, 1H), 7.49-7.46 (m, 2H), 7.45-7.31 (m, 4H), 5.11 (t, J=5.69 Hz, 1H), 4.50 (d, J=5.79 Hz, 2H), 3.29 (s, 3H); MS (ES) 473.3 [M+H]+ and 495.0 [M+Na]+.

Provenance & Evidence