[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].C(N(CC)C(C)C)(C)C.[CH3:21][O:22][CH2:23]Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.Cl>[CH3:11][O:10][C:6]1[C:3]([CH:4]=[O:5])=[C:2]([O:1][CH2:21][O:22][CH3:23])[CH:9]=[CH:8][CH:7]=12-Hydroxy-6-methoxybenzaldehyde (200 mg, 1.31 mmol) was placed in a 20 mL reaction vessel, and dissolved in 3.9 mL of dry dichloromethane. To the solution were added N,N-diisopropylethylamine (0.70 mL, 4.0 mmol), 4-dimethylaminopyridine (20 mg, 0.16 mmol), and chloromethyl methyl ether (250 μL, 3.28 mmol). After being stirred at room temperature overnight, the reaction mixture was diluted with 70 mL of ethyl acetate and 15 mL of 1N HCl, and extracted. The extract was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a pale yellow oil (224.4 mg, 87%).
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