Water → HCID 59633941, Verbindung

HRID 1615078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615078
[CH2:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=1)[CH:2]=[CH2:3].[OH2:15].C[N+]1([O-])CC[O:20]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C.[Os](=O)(=O)(=O)=O>[OH:15][CH:2]([CH2:3][OH:20])[CH2:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 59633949HCID 59633949, Verbindung2×

Produkt 1

HCID 59633941HCID 59633941, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixed solution of ethyl 4-allylpyridin-2-carboxylate (0.28 g) prepared in (1) in acetonitrile (9.0 mL)/water (3.0 mL) were added 4-methylmorpholine N-oxide (0.34 g) and aqueous 4% osmium tetraoxide (0.40 mL). The reaction mixture was stirred at RT for 12 hr. An excess amount of saturated aqueous Na2S2O3 was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: ethyl acetate/methanol=10/1) to give the title compound (0.25 g, 77%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography (Developing solvent: ethyl acetate/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-0b56a794fab940c6b790fa0e4feafebe
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765739B2

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