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

HRID 659970Notes

Reaction equation

HRID 659970 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

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-toluenesulphonic acid in 50 ml of toluene are heated for 5 hours under reflux. The reaction mixture is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is 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. The organic phase is concentrated under reduced pressure and the residue is purified by recrystallisation from ethyl acetate/cyclohexane, giving 300 mg (42% of theory) of 4-[(2-fluoroethyl)amino]furan-2(5H)-one.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. washthe mixture is washed 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. concentrationThe organic phase is concentrated under reduced pressure
  7. customthe residue is purified by recrystallisation from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-071013e725fc411eb1470c33e71805d9
Source dataset
uspto-grants-2011_12
Patent number
US08084452B2

Reaction notes

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