Water → 3-(4'-Hydroxy-2-isobutyl-3'-naphthalen-1-ylmethyl-biphenyl-4-yl)-propionitrile

Participants

Reaction Conditions

Reaction Steps

2.55 ml (2.55 mmol, 3.00 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 367.3 mg (0.85 mmol) 3-(2-Isobutyl-4′-methoxy-3′-naphthalen-1-ylmethyl-biphenyl-4-yl)propionitrile (65) in 40 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 2 h at 0° C. and then for 14 h at r.t. The reaction mixture was then added to water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (hexanes/EtOAc (2+1)) yielded 334.9 mg (0.80 mmol, 93.91%) 3-(4′-Hydroxy-2-isobutyl-3′-naphthalen-1-ylmethyl-biphenyl-4-yl)-propionitrile (66) as an oily white solid. Rf (hexanes/EtOAc (2+1))=0.36. 1H-NMR (500 MHz, CDCl3): δ=0.56 (d, 6H, J=6.62 Hz, 2*CH3), 1.48 (m, 1H, CH), 2.26 (d, 2H, J=7.41 Hz, CH2), 2.58 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.89 (t, 2H, J=7.41 Hz, CH2CH2CN), 4.44 (s, 2H, CH2Naphthyl), 4.80 (s, br., 1H, OH), 6.83 (d, 1H, J=8.20 Hz), 6.85 (d, 1H, J=2.05 Hz), 6.96-7.00 (m, 3H), 7.04 (d, 1H, J=7.41 Hz), 7.25 (m, 1H), 7.36 (m, 1H), 7.44 (m, 2H), 7.73 (d, 1H, J=8.20 Hz), 7.83 (m, 1H), 8.03 (m, 1H). MS (EI): m/z=419 (2), 335 (14), 293 (22), 253 (8), 161 (18), 160 (100), 91 (18). HR-MS (EI): Calcd. for C30H29NO: 419.224914. Found: 419.225626.

Provenance & Evidence