[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=O)[CH3:11].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+].C[O-].[Na+].Cl>CO.O.CN(C)C=O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[O:1][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([CH3:11])[C:3]=2[CH:4]=1To a mixture of 1-(2-hydroxy-5-methoxyphenyl)ethanone (5.00 g), methyl bromoacetate (3.13 mL) and N,N-dimethylformamide (50 mL) was added potassium carbonate (12.5 g), and the mixture was stirred overnight at room temperature. Water was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a brown oil. To a solution (50 mL) of the obtained oil in methanol was added sodium methoxide (1.63 g), and the mixture was stirred with heating under reflux for 3 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (1.25 g, 19%) as a white solid.
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