Potassium Carbonate → 2-(Diallylamino)-1-(5-fluoro-2-thienyl)ethanone

HRID 1618976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618976
Br[CH2:2][C:3]([C:5]1[S:6][C:7]([F:10])=[CH:8][CH:9]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([NH:20][CH2:21][CH:22]=[CH2:23])[CH:18]=[CH2:19]>C(#N)C.C(OCC)(=O)C.O>[CH2:17]([N:20]([CH2:21][CH:22]=[CH2:23])[CH2:2][C:3]([C:5]1[S:6][C:7]([F:10])=[CH:8][CH:9]=1)=[O:4])[CH:18]=[CH2:19]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 31279DiallylamineHCID 597069472-Bromo-1-(5-fluorothiophen-2-yl)ethanone

Produkt 1

HCID 866978892-(Diallylamino)-1-(5-fluoro-2-thienyl)ethanoneAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-bromo-1-(5-fluorothiophen-2-yl)ethanone (13.28 g, 59.53 mmol) in acetonitrile (298 mL) at 0° C. under nitrogen is added potassium carbonate (10.70 g, 77.39 mmol) and diallylamine (9.54 mL, 77.39 mmol). The mixture is allowed to slowly warm to room temperature with stiffing over 16 hours then diluted with ethyl acetate (500 mL) and water (200 mL). The phases are separated and the aqueous phase extracted twice with ethyl acetate (100 mL). The combined organic extracts are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with hexanes/ethyl acetate (9:1) to give the title compound (12.45 g, 87%) as a yellow oil. ES/MS (m/e): 240 (M+H).

Aufarbeitung

  1. customThe phases are separated
  2. extractionthe aqueous phase extracted twice with ethyl acetate (100 mL)
  3. dry with materialThe combined organic extracts are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with hexanes/ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-164d894130fa459ba0056361aca63630
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772282B2

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