Malononitrile → HCID 58016904, compound

Participants

Reaction Steps

Put 84 g (0.32 mol) 2-(2-fluorophenyl)-2-hydroxy-1-(4-methoxyphenyl)ethanone and 32 g (0.48 mol) malononitrile in 153 ml THF. After stirring for five minutes, add 49 ml (36 g, 0.36 mol) triethylamine, with ice cooling. Stir the reaction mixture for 1 h with ice cooling. Then leave the reaction mixture to warm to room temperature and stir for 4 h at this temperature. After adding 1000 ml ethyl acetate, wash the organic phase five times with 300 ml water, dry over sodium sulphate and filter. Concentrate the filtrate by vacuum evaporation. Take up the residue in dichloromethane and purify by flash chromatography on silica gel (solvent: dichloromethane/methanol 70:1, then cyclohexane/ethyl acetate 2:1). 37 g (0.11 mol) of 2-(2-fluorophenyl)-2-hydroxy-1-(4-methoxyphenyl)ethanone thus recovered is again reacted with 14 g (0.03 mol) malononitrile and 21 ml (15 g, 0.15 mol) triethylamine in 67 ml THF in accordance with the above procedure. A total of 70 g (52% purity, 36% of theor.) of the target compound is obtained.

Provenance & Evidence