Water → Trifluoro-methanesulfonic acid 3-benzyl-4'-(2-Cyano-ethyl)-2'-isobutyl-biphenyl-4-yl ester

Participants

Reaction Conditions

Reaction Steps

0.10 ml (0.59 mmol, 1.8 eqv) triflic anhydride was added to a solution of 116.8 mg (0.32 mmol) 3-(3′-Benzyl-4′-hydroxy-2-Isobutyl-1,1′-biphenyl-4-yl)propanenitrile (25) in 5 ml pyridine at 0° C. The resulting mixture was stirred at 0° C. for 30 min and then at rt for 18 h. After that, water was added and the mixture was extracted with Et2O. The comb. org. fractions were washed with brine, dried over MgSO4 and evaporated. Column chromatography (Hexanes/EtOAc (1+1)) yielded 136.9 mg (0.27 mmol, 85%) 26 as a pale violet solid: Rf (Hexanes/EtOAc (1+1)) 0.59, 1H NMR (500 MHz, CDCl3) δ 0.64 (d, 6H, J=6.62 Hz), 1.51 (m, 1H), 2.31 (d, 2H, J=7.25 Hz), 2.61 (t, 2H, J=7.41 Hz), 2.93 (t, 2H, J=7.41 Hz), 4.07 (s, 2H), 7.03-7.08 (m, 4H), 7.13-7.21 (m, 4H), 7.24-7.31 (m, 3H); LRMS (EI) m/z 503 (10), 502 (36), 501 (100), 369 (17), 368 (45), 326 (14), 91 (43); HRMS (EI) Calcd. for C27H26F3NO3S: 501.158551. Found: 501.158983.

Provenance & Evidence