2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → HCID 76852879, compound

HRID 890478Notes

Reaction equation

HRID 890478 reaction equation
[F:1][C:2]([F:20])([F:19])/[C:3](/O)=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)=O.[CH2:21]([O:23][C:24](=[O:29])/[CH:25]=[C:26](\[NH2:28])/[CH3:27])[CH3:22]>C(#N)C>[CH2:21]([O:23][C:24](=[O:29])[C:25]1[C:3]([C:2]([F:20])([F:19])[F:1])=[CH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)=[N:28][C:26]=1[CH3:27])[CH3:22]

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 178520888HCID 178520888, compound

Product 1

HCID 76852879HCID 76852879, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile (35 ml) solution of (Z)-4,4,4-trifluoro-3-hydroxy-1-(4-trifluoromethoxy-phenyl)-but-2-en-1-one (2.9 g, 10 mmol) was added ethyl-3-aminocrotonate (2.5 g, 19 mmol) under an argon atmosphere. The mixture was heated at reflux for 12 h. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, n-heptane/ethyl acetate) to yield 1.9 g (4.8 mmol, 50%) of the title compound as yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography (silica gel, n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-8dbd7e0aeea94aa7b47324ef216c2b87
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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