[N+:1]([C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][O:18][CH3:19])([CH3:16])[CH2:8][C:7]2=[O:20])([O-:3])=[O:2].CO.[BH4-].[Na+]>O>[N+:1]([C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][O:18][CH3:19])([CH3:16])[CH2:8][CH:7]2[OH:20])([O-:3])=[O:2]To 10 g of 6-nitro-2-methoxymethyl-2,5,7,8-tetramethylchroman-4-one, 100 ml of methanol was added and 1.3 g of sodium borohydride was added at 0° C., followed by stirring at 0° C. for one hour. The reaction solution was poured into water and then extracted with ethyl acetate. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, 10.1 g of the objective compound was obtained.
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