[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH3:17])=[N:14]2)=[CH:9][CH:8]=1)[CH3:5].[Se](=O)=[O:19]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH:17]=[O:19])=[N:14]2)=[CH:9][CH:8]=1)[CH3:5]To a solution of (R)-7-(1-methoxypropan-2-yloxy)-2-methylquinoline (0.22 g, 0.96 mmol) in dioxane (7 mL) and water (0.07 mL) was added selenium dioxide (0.13 g, 1.2 mmol) and the resultant mixture heated at reflux for 2 hours. The cooled reaction mixture was filtered through a plug of Celite® to remove solids, rinsing with dichloromethane. The filtrate was concentrated under reduced pressure and purified by normal phase chromatography on silica gel (10-20% ethyl acetate/hexanes) to afford the title compound (0.11 g, 46%).
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