2,6-Lutidine → 5,7-Difluoroquinoline-6-carbaldehyde

HRID 69137

Reaktionsgleichung

Reaktionsgleichung von HRID 69137
[F:1][C:2]1[C:11]([CH:12]=C)=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:24].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[C:11]([CH:12]=[O:24])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

7

Edukt 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 579173805,7-Difluoro-6-vinyl-quinoline

Produkt 1

HCID 579172825,7-Difluoroquinoline-6-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

5,7-Difluoro-6-vinyl-quinoline (iv) (614 mg, 3.21 mmol) was dissolved in dioxane (1.7 mL) and water (0.6 mL). 2,6-lutidine (0.761 mL, 6.42 mmol), sodium periodate (2.75 g, 12.85 mmol) and osmium tetroxide (653 mg, 0.064 mmol) were added to the previous solution. The RM was stirred at rt for 15 min. A precipitate was formed. Water was added to the RM and it was extracted twice with EtOAc. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by MPLC with Hexane and EtOAc to give the title compound as a white solid (tR 1.2 min (conditions 2), MH+=244, 1H-NMR in DMSO-d6: 10.36 (s, 1H); 9.15 (s, 1H); 8.65 (d, 1H); 7.79 (d, 1H); 7.69 (dd, 1H)).

Aufarbeitung

  1. customA precipitate was formed
  2. extractionwas extracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed
  6. customThe residue was purified by MPLC with Hexane and EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-f4c19fafe01e46b9b818cb859af5ec65
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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