[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:22]2[CH2:26][CH:25]([CH2:27][CH2:28][CH2:29][OH:30])[O:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C(OCC)C>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:22]2[CH2:26][CH:25]([CH2:27][CH2:28][CH:29]=[O:30])[O:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]After dissolving pyridinium chlorochromate (PCC; 2.249 g, 10.435 mmol) and 70-230 mesh SiO2 (2.748 g) in 25 mL of methylene chloride, 3-[3-(3,4-dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propan-1-ol (1.374 g, 5.217 mmol) dissolved in 2 mL of methylene chloride was added. After the reaction was continued for about 6 hr, 10 mL of diethyl ether was added and the reaction mixture was filtered through a cellite bed. After removing all the solvent and purifying by column chromatography on silica gel (hexane/ethyl acetate=1.5/1, v/v), 0.72 g (51.6%) of the target compound was obtained.
Loading…
