Reaction Steps
To a flame-dried and nitrogen filled Schlenk vessel were added Pd(OAc)2 (6.7 mg, 0.030 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.3 mg, 0.045 mmol), t-BuONa (115.4 mg, 1.2 mmol), and p-methoxyphenyl chloride (142.1 mg, 1.0 mmol)) in 1.5 mL of toluene sequentially. After being stirred for about 2 min at room temperature, propiophenone (160.9 mg, 1.2 mmol) in 1.5 mL of toluene were added. The resulting mixture was heated at 110° C. with a preheated oil bath. After 17.5 h, the reaction was complete as monitored by GC. The reaction mixture was then cooled and quenched with 10 mL of Et2O. After transferring the mixture into separatory funnel, the reactor was further washed with 10 mL of Et2O and 10 mL of HCl aqueous solution (5%). The combined mixture was extracted with Et2O (10 mL×2), washed with 20 mL of saturated NaHCO3 aqueous solution, and dried over anhydrous Na2SO4. Filtration, evaporation, and purification by chromatography (petroleum ether/ethyl acetate=80/1) on silica gel afforded 2-(4′-Methoxyphenyl)-1-phenyl-1-propanone (209.4 mg, 87%) as a liquid: 1H NMR (300 MHz, CDCl3) δ 8.00-7.92 (m, 2H, ArH), 7.52-7.43 (m, 1H, ArH), 7.42-7.35 (m, 2H, ArH), 7.24-7.18 (m, 2H, ArH), 6.86-6.80 (m, 2H, ArH), 4.65 (q, J=6.9 Hz, 1H, CH), 3.75 (s, 3H, OCH3), 1.52 (d, J=6.9 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 200.5, 158.4, 136.5, 133.4, 132.6, 128.73, 128.69, 138.4, 114.3, 55.1, 46.9, 19.5; IR (neat) v (cm−1) 3061, 2972, 2931, 2836, 1682, 1609, 1596, 1511, 1448, 1302, 1248, 1221, 1178, 1034, 1002; MS (70 eV, EI) m/z (%): 240 (M+, 4.46), 135 (100).
