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To a suspension of 136.8 mg (0.26 mmol) 3-(3′,3″-Dibenzyl-4″-hydroxy-2-isobutyl-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (28) and 184.9 mg (1.34 mmol, 5.2 eqv) K2CO3 in 12 ml acetone, 0.17 ml (2.69 mmol, 10.3 eqv) chloroacetonitrile was added. The resulting mixture was stirred for 40 h at 55° C. and then added to 40 ml of a mixture of brine/water (1+1). After extraction with EtOAc the combined org. fractions were washed with brine, dried over MgSO4 and evaporated. Column chromatography (Hexanes/EtOAc (2+1)) yielded 144.9 mg (0.25 mmol, 97%) 29 as a colorless oil: Rf (Hexanes/EtOAc (2+1)) 0.33; 1H NMR (500 MHz, CDCl3) δ 0.70 (d, 6H, J=6.62 Hz), 1.64 (m, 1H), 2.44 (d, 2H, J=7.41 Hz), 2.62 (t, 2H, J=7.41 Hz), 2.94 (t, 2H, J=7.41 Hz), 3.92 (s, 2H), 3.94 (s, 2H), 4.71 (s, 2H), 6.92 (m, 3H), 7.03-7.18 (m, 14H), 7.20-7.26 (m, 2H); 13C NMR (125 MHz, CDCl3) δ 19.38, 21.04, 22.39, 29.53, 31.33, 35.96, 39.11, 42.02, 53.96, 111.86, 115.18, 119.18, 125.39, 125.79, 126.07, 127.27, 128.27, 128.41, 128.52, 128.64, 128.76, 129.86, 129.94, 130.31, 130.55, 131.64, 132.33, 136.32, 136.78, 137.69, 139.77, 140.19, 140.88, 140.89, 141.40, 149.00, 153.60; LRMS (EI) m/z 575 (2), 574 (5), 535 (1), 501 (1), 446 (2), 409 (15), 408 (50), 369 (13), 91 (100); HRMS (EI) Calcd. for C41H38N2O: 574.298413. Found: 574.298309.
