Water → 3-(3',3''-Dibenzyl-4''-hydroxy-2-isobutyl-1,1':4',1''-terphenyl-4-yl)propanenitrile

Participants

Reaction Conditions

Reaction Steps

0.90 ml (0.90 mmol, 3 eqv) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 164.3 mg (0.30 mmol) 3-(3′,3″-Dibenzyl-2-isobutyl-4″-methoxy-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (27) in 7 ml dry CH2Cl2 at 0° C. via syringe. After that, the solution was stirred for 2 h at 0° C. and then for 4 h at rt. 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 137.5 mg (0.26 mmol, 86%) 28 as a colorless oil: Rf (Hexanes/EtOAc (2+1)) 0.35; 1H NMR (500 MHz, CDCl3) δ 0.67 (d, 6H, J=6.62 Hz), 1.61 (m, 1H), 2.40 (d, 2H, J=7.09 Hz), 2.58 (t, 2H, J=7.41 Hz), 2.91 (t, 2H, J=7.41 Hz), 3.89 (s, 2H), 3.93 (s, 2H), 5.57 (s, 1H), 6.74 (d, 1H, J=8.04 Hz), 6.90 (m, 2H), 6.99-7.26 (m, 16H); LRMS (EI) m/z 536 (19), 535 (46), 501 (10), 446 (9), 369 (21), 91 (100), 78 (12), 76 (10); HRMS (EI) Calcd. for C39H37NO: 535.287514. Found: 535.287420.

Provenance & Evidence