Acetic Acid → Ethyl-3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

HRID 1766344Notes

Reaction equation

HRID 1766344 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=O.O.S([O-])([O-])(=O)=O.[Mg+2].C(O)(=O)C>C(O)C>[CH2:19]([O:18][C:12](=[O:17])[CH:13]=[C:14]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[CH3:16])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 8868Ethyl AcetoacetateHCID 16211255Kieserite

Product 1

HCID 68427624Ethyl-3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Trifluoromethylaniline (2.50 g, 15.5 mmol) and ethyl acetoacetate (2.32 g, 17.8 mmol) are dissolved in absolute ethanol in a 500 ml round bottom flask equipped with a stir bar and a reflux condenser. Magnesium sulphate monohydrate (2.58 g, 18.6 mmol) and glacial acetic acid (14 mg, 0.23 mmol) are added. The suspension is stirred rigorously at reflux for 16 hours under an argon atmosphere. The crude reaction mixture is cooled to room temperature, filtered and concentrated in vacuo to give an oil. The oil is chromatographed over silica gel with cyclohexane/ethyl acetate mixtures as eluent to yield a pale yellow oil which is analytically pure.

Workup

  1. customequipped with a stir bar and a reflux condenser
  2. temperatureat reflux for 16 hours under an argon atmosphere
  3. customThe crude reaction mixture
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThe oil is chromatographed over silica gel with cyclohexane/ethyl acetate
  8. customto yield a pale yellow oil which

Sources & evidence

ORD record
ord-7f00199965414111ab6ff77f03a05067
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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