Sodium Thiosulfate → HCID 59631569, Verbindung

HRID 1431758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431758
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH:19]=C)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:25]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH:19]=[O:25])=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 59631216HCID 59631216, Verbindung

Produkt 1

HCID 59631569HCID 59631569, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a solution of 7-fluoro-3-methyl-2-(pyridin-2-yl)-4-vinylquinoline (1.53 g, 5.79 mmol) in acetone (30 mL) and water (7.50 mL) were added N-methylmorpholine-N-oxide (2.034 g, 17.37 mmol) and osmium tetroxide (0.074 g, 0.289 mmol). The reaction was stirred at 23° C. for 18 h. Upon completion, 10% aqueous sodium thiosulfate was added and the reaction was stirred for an additional 10 minutes. The reaction mixture was then concd, and the dihydroxylated product was extracted with EtOAc (twice) and DCM (twice). The combined organics were dried over magnesium sulfate and concd, and the resulting residue was resolubilized in 30 mL 4:1 acetone:water and 3 mL dioxane. To this solution sodium periodate (3.10 g, 14.47 mmol) was added, and stirring continued at 23° C. for 2 h. Upon completion, the organic solvents were removed under vacuum, and the afforded crude material was partitioned between EtOAc and water. The organic phase was dried over magnesium sulfate and concd, and purification by column chromatography (silica; 0-70% EtOAc in hexanes yielded 7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline-4-carbaldehyde as a white amorphous solid. Mass Spectrum (ESI) m/e=367.1 (M+1).

Aufarbeitung

  1. stirringthe reaction was stirred for an additional 10 minutes
  2. extractionthe dihydroxylated product was extracted with EtOAc (twice) and DCM (twice)
  3. dry with materialThe combined organics were dried over magnesium sulfate and concd
  4. stirringstirring
  5. waitcontinued at 23° C. for 2 h
  6. customUpon completion, the organic solvents were removed under vacuum
  7. customthe afforded crude material
  8. customwas partitioned between EtOAc and water
  9. dry with materialThe organic phase was dried over magnesium sulfate and concd, and purification by column chromatography (silica

Quellen und Nachweise

ORD-Eintrag
ord-e90ff463049e4e11b5fcc1759f72c16e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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