Sodium Cyanide → (3'-Benzyloxybiphenyl-2-yl)acetonitrile

Participants

Reaction Steps

To a stirred solution of 2-chloromethyl-3′-benzyloxybiphenyl from Step A (188 mg, 0.61 mmol) in EtOH (4 mL) was added a solution of NaCN (60 mg, 1.22 mmol) in water (4 mL). The resulting solution was heated to reflux for 12 h, stood at ambient temperature for 48 h, then concentrated under reduced pressure. The residue was partitioned between sat. aq. NaHCO3 (10 mL) and CH2Cl2 (20 mL). The aqueous layer was extracted further with CH2Cl2 (2×10 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with a gradient of 2-10% EtOAc in hexane to give the titled product.

Provenance & Evidence