Water → 1-[2-(1,3-Dioxolan-2-yl)ethyl]-6-fluoroquinoxalin-2(1H)one

HRID 1847086

Reaktionsgleichung

Reaktionsgleichung von HRID 1847086
[H-].[Li+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[N:7]2.Br[CH2:16][CH2:17][CH:18]1[O:22][CH2:21][CH2:20][O:19]1.O>CN(C)C=O>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[CH2:17][CH2:16][N:10]1[C:11]2[C:6](=[CH:5][C:4]([F:3])=[CH:13][CH:12]=2)[N:7]=[CH:8][C:9]1=[O:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 62714Lithium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 126863866-Fluoro-1,2-dihydroquinoxalin-2-one

Produkt 1

HCID 867250091-[2-(1,3-Dioxolan-2-yl)ethyl]-6-fluoroquinoxalin-2(1H)oneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Lithium hydride (57 mg, 7.3 mmol) was added to a solution of 6-fluoroquinoxalin-2(1H)one (1 g, 6.0 mmol) in N,N-dimethylformamide (6 ml) under cooling on ice and the mixture was stirred at room temperature for 30 minutes. The mixture was cooled on ice again and a solution of 2-(2-bromoethyl)-1,3-dioxolane (0.88 ml, 7.3 mmol) in N,N-dimethylformamide (2 ml) was gradually added thereto and the mixture was stirred for 4 hours. Water was added thereto, the mixture was then extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 0.5 g (32%) of the title compound.

Aufarbeitung

  1. temperatureunder cooling on ice
  2. temperatureThe mixture was cooled on ice again
  3. stirringthe mixture was stirred for 4 hours
  4. extractionthe mixture was then extracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6d0acef788034ee3b21b7f58af07c8d3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952010B2

Verknüpfte Notizen

Wird geladen…