Ammonium Chloride → HCID 18353681, compound

Participants

Reaction Steps

To lithium aluminium hydride (0.63 g, 16.5 mmol) in diethyl ether (12 ml) was added 4-(3,4-dichlorophenyl)azetidin-2-one (1 g, 4.6 mmol). The mixture was refluxed under argon for 4 h then cooled and 20% aqueous ammonium chloride solution (3 ml) added. Diethyl ether (30 ml) was added and the mixture filtered, and the insoluble material washed with more diethyl ether (20 ml). The combined filtrates were dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil, (0.76 g). A portion of this material (0.55 g) was purified by column chromatography on silica gel eluting with 2-10% (9:1 MeOH/0.880 NH3) in dichloromethane gave the title compound, (0.44 g, 65%). δH (CDCl3) 2.0 (1H, bs), 2.3 (1H, m), 2.55 (1H, m), 3.34 (1h, m), 3.75 (1H, m), 4.9(1H, t), 7.2 (1H, dd), 7.4(1H, d), 7.5 (1H, d).

Provenance & Evidence