Acetonitrile → HCID 53640530, compound

Participants

Reaction Steps

A suspension of potassium hydroxide (85%, 260 mg, 3.9 mmol) in CH3CN (25 mL) was heated to reflux and (Z)-1,2-Diphenyl-1-(4-formylphenyl)-1-butene (4a) (Willson J. Med. Chem. 1994, 37, 1550–1552) (1.0 g, 3.18 mmol) was added in portions. After refluxing 5 min, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 15% EtOAc/hexanes) to give nitrile (4b) as a white solid (616 mg, 57%): 1H NMR (CDCl3) δ 7.39–7.07 (m, 13H), 6.91 (d, J=8.4 Hz, 2H), 5.69 (d, J=16.9 Hz, 1H), 2.48 (q, J=7.3 Hz, 2H), 0.94 (t, J=7.3 Hz, 3H); HRMS calcd. for C25H21N (M+H+) 335.1674; found 335.1679.

Provenance & Evidence