Ethanol → HCID 12526834, compound

Participants

Reaction Steps

To a solution consisting of 1-biphenyl-4-yl-2-bromo-ethanone (412 mg. 1.5 mmol) and EtOH (6 mL) was added NaN3 (107 mg, 1.6 mmol) at rt. The mixture was stirred at rt for 2 h and then cooled to 0° C. NaBH4 (61 mg, 1.6 mmol) was added and the mixture stirred for 45 min. A mixture (black slurry) of CuSO4.5H2O (37 mg)/NaBH4 (28 mg) in MeOH 2 mL) was prepared by adding the NaBH4 to CuSO4.5H2O in MeOH at 0° C. This slurry was poured into the reaction mixture. The reaction vessel was allowed to gradually warm to rt. An additional amount of NaBH4 (28 mg) was added 30 min after the addition of the slurry. The reaction was stirred at rt for 2 h. The mixture was filtered through a pad of celite, adhered to silica gel (7-8 g) and purified (FCC) to give the title compound (256 mg, 80%).

Provenance & Evidence