[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=C(C=C)[CH:8]=[CH:7]2.C[N+]1([O-])CC[O:18]CC1.[CH3:22][C:23]([CH3:25])=[O:24].O>ClCCl.O=[Os](=O)(=O)=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:22]([CH:23]([OH:24])[CH2:25][OH:18])[CH:8]=[CH:7]2To 8-bromo-2-vinylquinoline (0.886 g, 3.78 mmol) in acetone/H2O (8 mL/2 mL) was added 4-methylmorpholine N-oxide (1.06 g, 4.54 mmol) followed by OsO4 (0.5 mL, 2.5% in t-BuOH). The reaction mixture was stirred for two hours at ambient temperature then diluted with dichloromethane. The organic layer was washed with saturated sodium sulfate and brine and concentrated to give crude product.
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