[CH3:1][C:2]1([CH3:17])[O:16][CH2:15][C:5]2([CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=O)[CH2:4][O:3]1.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C.O>[OH:20][N:19]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C:5]21[CH2:15][O:16][C:2]([CH3:17])([CH3:1])[O:3][CH2:4]2A suspension of 1 g of 2,2-dimethylspiro[1,3-dioxane-5,2′-inden]-1′(3′H)-one, 329 mg of hydroxylamine hydrochloride, and 388 mg of sodium acetate in 5 ml of ethanol was stirred for 12 hours. Then, 1.2 ml of triethylamine was added thereto, followed by stirring at room temperature for 3 days and further stirring at 50° C. for 1 hour. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.0 g of N-hydroxy-2,2-dimethylspiro[1,3-dioxane-5,2′-inden]-1′(3′H)-imine.
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