Water → 4-[(2-fluoroethyl)amino]furan-2(5H)-one

HRID 425748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425748
O.Cl.[F:3][CH2:4][CH2:5][NH2:6].[CH2:7]1[C:12](=[O:13])[O:11][CH2:10][C:8]1=O.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:3][CH2:4][CH2:5][NH:6][C:8]1[CH2:10][O:11][C:12](=[O:13])[CH:7]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 517045Sodium AcetateHCID 521261Tetronic acid

Produkt 1

HCID 552864454-[(2-fluoroethyl)amino]furan-2(5H)-oneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

On a water separator, 550 mg (4.97 mmol) of 2-fluoroethylamine hydrochloride, 547 mg (5.47 mmol) of tetronic acid, 408 mg (4.97 mmol) of sodium acetate and 9 mg (0.05 mmol) of 4-toluene-sulphonic acid in 50 ml of toluene are heated under reflux for 5 hours. The reaction mixture is concentrated under reduced pressure and then taken up in ethyl acetate and washed with 1 N aqueous sodium hydroxide solution. The aqueous phase is extracted repeatedly with ethyl acetate and the combined organic phase is dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue by recrystallization from ethyl acetate/cyclohexane gives 300 mg (42% of theory) of 4-[(2-fluoroethyl)amino]furan-2(5H)-one.

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. washwashed with 1 N aqueous sodium hydroxide solution
  4. extractionThe aqueous phase is extracted repeatedly with ethyl acetate
  5. dry with materialthe combined organic phase is dried over sodium sulphate
  6. customConcentration of the organic phase under reduced pressure and purification of the residue
  7. customby recrystallization from ethyl acetate/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-e65a4420b6b243a48f7060adf994a25b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106211B2

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