反应详情

温度

80 °C

167.7 mg (0.33 mmol) 4′-(2-Cyanoethyl)-3-benzyl-2′-isobutyl-1,1′-biphenyl-4-yl-trifluoromethanesulfonate (26), 158.7 mg (0.49 mmol, 1.5 eqv) 2-(3-Benzyl-4-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (23) and 58.8 mg (50.9 pmol, 0.15 eqv) Pd(Ph3P)4 were dissolved in 10 ml DME/EtOH (9+1). 0.33 ml (0.66 mmol, 2 eqv) of a 2 M aq. Na2CO3-solution was added to this yellow solution and the resulting mixture was heated at 80° C. for 8 h. After concentrating the mixture in vacuo the residue was taken up in water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (Hexanes/EtOAc (3+1)) yielded 165.6 mg (0.30 mmol, 91%) (27) as a clear oil: Rf (Hexanes/EtOAc (3+1)) 0.30; 1H NMR (500 MHz, CDCl3) δ 0.69 (d, 6H, J=6.62 Hz), 1.63 (m, 1H), 2.43 (d, 2H, J=7.41 Hz), 2.61 (t, 2H, J=7.57 Hz), 2.93 (t, 2H, J=7.57 Hz), 3.82 (s, 3H), 3.93 (s, 4H), 6.85 (d, 1H, J=8.36 Hz), 6.94 (m, 2H), 7.02-7.22 (m, 16H); LRMS (EI) m/z 549 (3), 501 (2), 446 (11), 383 (5), 335 (6), 293 (9), 256 (14), 215 (16), 214 (100), 199 (16), 160 (49), 91 (47); HRMS (EI) Calcd. for C40H39NO: 549.303164. Found: 549.302298.

1. concentrationAfter concentrating the mixture in vacuo the residue
2. extractionextracted with CH2Cl2
3. dry with materialfractions were dried over MgSO4
4. customevaporated