[H-].[Na+].[CH3:3][CH:4]([CH:7]=[CH2:8])[CH2:5][OH:6].[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12]Br.[Cl-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12][O:6][CH2:5][CH:4]([CH3:3])[CH:7]=[CH2:8]Sodium hydride (60 wt %, 928 mg) was added to a solution of 2-methyl-3-buten-1-ol (2 g) in DMF (30 mL) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. Bromoacetaldehyde dimethyl acetal (5.45 mL) was added dropwise to the reaction solution at the same temperature. The reaction solution was stirred for 16 hours with gradual heating to room temperature. Ethyl acetate and aqueous sodium chloride were added to the reaction solution, and the organic layer was separated. The same operation was performed on the same scale. The combined organic layers were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (4.92 g).
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