Butyrophenone → HCID 58951958, compound

Participants

Reaction Steps

To a solution of 200 mg (0.46 mmol) 4-iodo-1-trityl-imidazole in 3 ml anhydrous dichloromethane was added at ambient temperature 0.16 ml (0.48 mmol) 3M ethyl magnesium bromide in diethyl ether. The mixture was stirred for 1 hour then a solution of 55 mg (0.37 mmol) 1-phenyl-butan-1-one in 0.1 ml anhydrous dichloromethane was added in one portion and the reaction mixture was stirred for 16 hours. Saturated aqueous ammonium chloride (5 ml) was then added to the reaction mixture and the whole was extracted with dichloromethane (3×5 ml). The organic phase was washed with water (3×5 ml) then brine (3×5 ml), dried over MgSO4, concentrated and purified by preparative HPLC to give 90 mg rac-1-phenyl-1-(1-trityl-1H-imidazol-4-yl)-butan-1-ol as colourless oil: MS (ISP): 459.0 ((M+H)+.); 1H-NMR (CDCl3): 0.80 (3H, t, CH3), 1.30 (2H, m), 2.05 (2H, m, CH2), 3.45 (1H, s, br, OH), 6.70 (1H, s), 7.05-7.45 (21H, m).

Provenance & Evidence