[OH:1][CH:2](CO)[CH2:3][C:4]1[C:5]([O:17][CH3:18])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]2=[O:16].O.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.CO.C(OCC)(=O)C>[CH3:18][O:17][C:5]1[C:4]([CH2:3][CH:2]=[O:1])=[C:13]2[C:8]([C:9](=[O:16])[CH2:10][C:11]([CH3:14])([CH3:15])[O:12]2)=[CH:7][CH:6]=1
145 mg of 8-(2,3-dihydroxypropyl)-7-methoxy-2,2-dimethyl-4-oxochroman was dissolved in 3 ml of tetrahydrofuran and 4 ml of methanol. Thereafter, 7 ml of water containing 0.22 g of sodium metaperiodate was added to the reaction solution while cooling on ice, and the obtained mixture was then stirred at room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate, and then washed with a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then filtered. The organic layer was then concentrated under a reduced pressure, so as to obtain 120 mg of (7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehyde. This compound was used in the following reaction without further purification.
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