Aluminium lithium hydride → HCID 90460898, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 1-(4-cyanophenyl)-1H-imidazole-5-carboxylate (50 mg, 0.21 mmol, 1.00 equiv) in anhydrous tetrahydrofuran (10 mL) maintained under nitrogen at −40° C. was added LiAlH4 (24 mg, 0.63 mmol, 3.05 equiv) in portions. The reaction was stirred at −40° C. for 1 h and then quenched by the addition of 2 mL of saturated aqueous NH4Cl solution. The solid was removed by filtration and the filtrate was concentrated under vacuum. The residue was purified on a silica gel column eluted with 3.0-6.7% of methanol in dichloromethane to yield 36 mg (87%) of 4-(5-(hydroxymethyl)-1H-imidazol-1-yl)benzonitrile as a white solid. 1H-NMR (300 MHz, CDCl3): δ 10.11 (s, 1H), 8.07 (d, J=6.3 Hz, 2H), 7.85 (d, J=6.3 Hz, 2H), 7.77-7.72 (m, 4H), 7.24 (s, 1H), 4.63 (d, J=7.5 Hz, 2H) ppm. LCMS (method C, ESI): RT=0.25 min, m/z=200.0 [M+H]+.

Provenance & Evidence