[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17]Br)[CH3:14].O>CN(C=O)C>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH3:14]To a solution of 1-(4-hydroxyphenyl)ethanone (1.00 g, 7.34 mmol) in N,N′-dimethylformamide (24 mL), sodium hydride (purity 50%) (380 mg, 8.07 mmol), and bromoacetaldehyde diethyl acetal (1.30 mL, 8.81 mmol) were added under ice-cold conditions and stirred at 120° C. overnight. Under ice-cold conditions, the reaction solution was added water, and extracted with diethylether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (2.47 g (yield >100%)) was obtained as a yellow oil.
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