반응 #682534

반응 방정식

o-methoxyphenyl chloride

propiophenon

t-BuONa

→

2-(2′-Methoxyphenyl)-1-phenyl-1-propanone

수율 82.7%

용매

toluene

반응 조건

후처리

1. 1
   기타This reaction is carried out in the same manner as the reaction in example 3
2. 2
   기타at 110° C.
3. 3
   기타for 16 h

실험 절차

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are o-methoxyphenyl chloride (144.1 mg, 1.0 mmol), propiophenon (161.3 mg, 1.2 mmol), palladium acetate (6.7 mg, 0.030 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.4 mg, 0.045 mmol), t-BuONa (115.5 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 16 h. 2-(2′-Methoxyphenyl)-1-phenyl-1-propanone (198.8 mg) was obtained with a yield of 80% as liquid. 1H NMR (300 MHz, CDCl3) δ 8.04-7.98 (m, 2H, ArH), 7.50-7.42 (m, 1H, ArH), 7.41-7.33 (m, 2H, ArH), 7.24-7.13 (m, 2H, ArH), 6.92-6.86 (m, 2H, ArH), 5.13 (q, J=6.9 Hz, 1H, CH), 3.87 (s, 3H, OCH3), 1.51 (d, J=6.9 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 201.2, 155.6, 136.4, 132.4, 130.0, 128.4, 128.2, 127.9, 120.9, 110.7, 55.3, 40.2, 17.5; IR (neat) v (cm−1) 3063, 2974, 2933, 2871, 2837, 1682, 1597, 1584, 1493, 1449, 1371, 1326, 1291, 1245, 1222, 1182, 1113, 1061, 1050, 1028, 1002; MS (70 eV, EI) m/z (%): 241 (M++1, 1.81), 240 (M+, 9.60), 135 (100).

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