[H-].[Na+].Br[CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:15][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[CH:12][CH:11]=1Sodium hydride (purity: 55%, 700 mg) and 1-bromo-3-methylbutane (2.56 mL) were added to a solution of 4-bromobenzylalcohol (2.0 g) in N,N-dimethylformamide (40 mL) under ice-cooling, and the mixture was stirred at room temperature for five hours. A saturated ammonium chloride solution was added to the reaction solution, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→50:1→30:1) to give the title compound (2.31 g, 85%).
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