[CH2:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[CH2:2][CH:3]=[CH2:4].[OH2:13].C[N+]1([O-])CC[O:18]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:13][CH:3]([CH2:4][OH:18])[CH2:2][CH2:1][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1
To a mixed solution of 4-but-3-enyl-pyridine-2-carbonitrile (0.17 g) prepared in (1) in acetone (4 mL)/water (2 mL) were added 4-methylmorpholine N-oxide (0.37 g) and aqueous 4% osmium tetraoxide (0.67 g). The reaction mixture was stirred at RT for 12 hr. Saturated aqueous Na2S2O3 was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=15/1) to give the title compound (0.15 g, 72%).
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