تفاعل #54108

معادلة التفاعل

Na2CO3

Trifluoro-methanesulfonic acid 4-(2-Cyanoethyl)-2-isobutyl-phenyl ester

4-(2-cyanoethyl)-2-isobutylphenyl trifluoromethanesulfonate

3-Benzyl-4-methoxy-benzene-1-boronic acid

3-benzyl-4-methoxy-benzene-1-boronic acid

→

24

المردود 52.1%

3-(3′-benzyl-2-isobutyl-4′-methoxy-1,1′-biphenyl-4-yl)propanenitrile

المردود 52.1%

المذيبات

DME EtOH

ظروف التفاعل

المعالجة

1. 1
   تركيزAfter concentrating the mixture in vacuo the residue
2. 2
   استخلاصextracted with CH2Cl2
3. 3
   تجفيفfractions were dried over MgSO4
4. 4
   أخرىevaporated

الإجراء التجريبي

490 mg (1.46 mmol) Trifluoro-methanesulfonic acid 4-(2-Cyanoethyl)-2-isobutyl-phenyl ester (6), 505 mg (2.09 mmol, 1.4 eqv) crude 3-Benzyl-4-methoxy-benzene-1-boronic acid (22) and 169.4 mg (0.15 mmol, 0.1 eqv) Pd(Ph3P)4 were dissolved in 20 ml DME/EtOH (9+1). 1.46 ml (2.92 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 17 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 290.8 mg (0.76 mmol, 52%) 24 as a clear oil: Rf (Hexanes/EtOAc (3+1)) 0.34; 1H NMR (400 MHz, CDCl3) δ 0.63 (d, 6H, J=6.70 Hz), 1.55 (m, 1H), 2.35 (d, 2H, J=7.33 Hz), 2.57 (t, 2H, J=7.45 Hz), 2.88 (t, 2H, J=7.45 Hz), 3.79 (s, 3H), 3.92 (s, 2H), 6.82 (d, 1H, J=8.34 Hz), 6.92 (d, 1H, J=2.15 Hz), 6.96-7.20 (m, 9H); LRMS (EI) m/z 383 (13), 335 (15), 293 (23), 214 (17), 187 (21), 161 (20), 160 (100), 145 (35), 144 (35), 105 (50), 91 (58), 77 (11); HRMS (EI) Calcd. for C27H29NO: 383.224914. Found: 383.225267.

المصدر