Potassium Carbonate → HCID 67456227, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-hydroxy-4-phenylbenzonitrile (0.600 g) in N,N-dimethylformamide (4.1 mL) was added potassium carbonate (0.850 g). Then 4-benzyloxy-1-bromobutane (0.703 mL) was added, and the resulting mixture was stirred at 50° C. for 26.5 hours. The reaction mixture was cooled to room temperature and then partitioned between diethyl ether (35 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue (1.25 g) was dissolved in tetrahydrofuran (13 mL) and added to an ice-cold suspension of lithium alminiumhydride (0.175 g) in tetrahydrofuran (18 mL), and the resulting mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature and then quenched by sequential addition of water (0.175 mL), 15% aqueous sodium hydroxide (0.175 mL) and water (0.175 mL). After addition of anhydrous sodium sulfate (10.4 g), the mixture was stirred at room temperature for 13 hours and the insoluble material was filtered out. The filtrate was concentrated under reduced pressure to give the title compound (1.21 g).

Provenance & Evidence