[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][CH2:9][CH:10]([OH:13])[CH2:11][OH:12])=[CH:3][CH:2]=1.[CH3:14][CH2:15][C:16](=O)[CH2:17][CH3:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:7]([O:8][CH2:9][CH:10]1[CH2:11][O:12][C:16]([CH2:17][CH3:18])([CH2:15][CH3:14])[O:13]1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1To a tetrahydrofuran (30 ml) solution of DL-α-O-benzyl glycerol (3 g, 16.5 mmol), 3-pentanone (17.5 ml, 165 mmol) and p-toluenesulfonic acid monohydrate (300 mg, 1.58 mmol) were added at room temperature and the mixture was stirred at the same temperature for 22 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (5 ml) was added to adjust pH to about 8. The generated precipitate was removed by filtration and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 3/1 gradient). A desired fraction was concentrated to obtain the title compound (2.77 g, 67.1% yield) as a colorless oil.
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