Water → HCID 59633980, compound

HRID 1615085Notes

Reaction equation

HRID 1615085 reaction equation
[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

Participants

7

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 59634012HCID 59634012, compound2×

Product 1

HCID 59633980HCID 59633980, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

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%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-9ca800461bb94f289ca040c2eb7b266a
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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