Sodium Hydroxide → HCID 58380954, compound

Participants

Reaction Steps

1-cyano-1-(4-fluorophenyl)cyclopent-3-ene (117, 1.4 g, 7.48 mmol) was dissolved in toluene (3.5 mL) and ethyl magnesium bromide (5 mL, 15 mmol, 3M in ether) added. After stirring for 2.5 hours, the reaction mixture was added dropwise to ice cold methanol (50 mL), followed by sodium borohydride (560 mg, 15 mmol). The mixture was warmed to room temperature and stirred overnight. The white suspension was treated with sodium hydroxide solution (aq, 1M, 125 mL) and then extracted with dichloromethane/isopropanol (3/1). The organic phase was washed with brine, dried over sodium sulphate and evaporated to give 1.2 g of a yellow oil. This was taken up in dichloromethane and extracted twice with dilute hydrochloric acid (2M). The combined aqueous layers were made basic with aqueous sodium hydroxide solution (5M) and re-extracted with dichloromethane/isopropanol (3/1). Drying over sodium sulphate and evaporation gave 348 mg of the desired product Rt=2.37 min (Method 2). Detected mass: 220.1 (M+H+).

Provenance & Evidence