Dimethyl Carbonate → Methyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoate

反応式

[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:20](=O)([O:23]C)[O:21][CH3:22]>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:19])[CH2:18][C:20]([O:21][CH3:22])=[O:23])=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

実験手順

To a stirring suspension of NaH (3.7 g, 154.2 mmol) in DMF (25 mL) was added 1-[4-(benzyloxy)phenyl]ethanone (7 g, 31 mmol) at −5° C. and stirred for 30 min, then dim ethyl carbonate (13.5 g, 150 mmol, dissolved in DMF) was added at −5° C. slowly (exothermic) and warmed slowly to RT, stirred at RT for overnight. Reaction mass was quenched with ice cold water and extracted with ethyl acetate, organic layer was washed with water and brine dried over Na2SO4. The organic layer was concentrated to give the product (7 g, Yield: 92%): 1H NMR (300 MHz, CDCl3): δ 7.84-7.87 (d, 2H), 7.28-7.35 (m, 5H), 6.94-6.96 (d, 2H), 5.07 (s, 2H), 3.89 (s, 2H), 3.68 (s, 3H)