Acetonitrile → HCID 58089020, compound

Participants

Reaction Steps

n-BuLi (1.6 M in hexanes, 146 mL, 234 mmol) was added dropwise at −78° C. to a solution of CH3CN (10.39 mL, 199 mmol) in THF (600 mL) and the reaction mixture was stirred for 30 min. A solution of ester (2) (30.0 g, 117 mmol) in THF (50 mL) was added and the mixture was further stirred for 30 min at −78° C. The reaction mixture was quenched at −78° C. by addition of aqueous NH4Cl (200 mL), diluted with EtOAc (500 mL), the organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 3-(3-(benzyloxy)phenyl)-3-oxopropanenitrile (3) as a pale yellow solid. Yield (25.0 g, 85%); 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 7.48-7.36 (m, 6H), 7.35-7.33 (m, 1H), 7.27-7.26 (m, 1H), 5.12 (s, 2H), 4.05 (s, 2H).

Provenance & Evidence