Aluminium lithium hydride → HCID 90456112, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of LiAlH4 (114 mg, 3.36 mmol, 3.00 equiv) in anhydrous THF (5 mL) maintained under nitrogen at −50° C. was added dropwise a solution of ethyl 4-(4-cyanophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-5-carboxylate (371 mg, 1.00 mmol, 1.00 equiv) in anhydrous THF (2 mL). The reaction was stirred at −50° C. for 1 h and then quenched by the addition of 1 mL of water. The resulting mixture was extracted with 4×20 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified on a silica gel column eluted with 0-50% of ethyl acetate in petroleum ether to give 110 mg (33%) of 4-(5-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)benzonitrile as a pale yellow solid. 1H-NMR (300 MHz, CDCl3): δ 7.92-7.85 (m, 2H), 7.71-7.65 (m, 3H), 5.39 (s, 2H), 4.79 (s, 2H), 3.56 (t, J=11.2 Hz, 2H), 0.94 (t, J=11.2 Hz, 2H), 0.01 (s, 9H) ppm. LCMS (method A, ESI): RT=1.27 min, m/z=330.0 [M+H]+.

Provenance & Evidence