Ethanol → HCID 67835619, compound

HRID 1196769Notes

Reaction equation

HRID 1196769 reaction equation
[F:1][CH:2]([C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])(=O)C.[NH4+:20].C(O)C.[Na]>C(O)(=O)C>[F:1][C:2](=[C:8]([NH2:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 517165Ammonium AcetateHCID 5360545SodiumHCID 12646284Ethyl 2-fluoro-3-oxo-3-phenylpropanoate

Product 1

HCID 67835619HCID 67835619, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.0 g of ethyl a-fluorobenzoylacetate and 7.0 g of ammonium acetate were added to 50 ml of ethanol, followed by dropwise addition of 6.0 g of acetic acid to this solution with stirring at room temperature. The mixed solution was further stirred under reflux for 4 hours and added to a cooled aqueous solution of sodium hydrogencarbonte. This aqueous mixture was extracted with 200 ml of diethyl ether, and the organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 5.5 g of ethyl 2-fluoro-3-amino-3-phenyl-2-propenoate.

Workup

  1. stirringThe mixed solution was further stirred
  2. temperatureunder reflux for 4 hours
  3. extractionThis aqueous mixture was extracted with 200 ml of diethyl ether
  4. washthe organic layer was washed with a sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-1caab7803b1d478381d25b6ffd1ba41c
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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