[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl.[BH4-].[Na+].[C:19](O)(=O)[CH2:20][C:21](CC(O)=O)(C(O)=O)O>CN(C)C=O.BrC(C)C.CO>[CH:20]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])([CH3:21])[CH3:19]To a solution of 2-hydroxybenzaldehyde (0.5 ml) in dimethylformamide (5 ml), 1.35 ml of 2-bromopropane and 1.98 g of potassium carbonate were added, and the reaction solution was stirred overnight at room temperature. To the reaction solution was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in methanol (5 ml), 362 mg of sodium borohydride was added under ice-cooling, and the reaction solution was stirred at room temperature for 30 minutes. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford the title compound as a colorless oil.
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