Water → 4-[(2-fluoroethyl)amino]furan-2(5H)-one
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]=1Participants
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 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.
Workup
- temperatureunder reflux for 5 hours
- concentrationThe reaction mixture is concentrated under reduced pressure
- washwashed with 1 N aqueous sodium hydroxide solution
- extractionThe aqueous phase is extracted repeatedly with ethyl acetate
- dry with materialthe combined organic phase is dried over sodium sulphate
- customConcentration of the organic phase under reduced pressure and purification of the residue
- customby recrystallization from ethyl acetate/cyclohexane
Sources & evidence
- ORD record
- ord-0899c35c276648e4bf2fc3e17911fa75
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404855B2
Reaction notes
Loading…