2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → 851070-23-0

HRID 890473Notes

Reaction equation

HRID 890473 reaction equation
[F:1][C:2]([F:19])([F:18])/[C:3](/O)=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[CH2:20]([O:22][C:23](=[O:28])/[CH:24]=[C:25](\[NH2:27])/[CH3:26])[CH3:21]>C(#N)C>[CH2:20]([O:22][C:23](=[O:28])[C:24]1[C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:27][C:25]=1[CH3:26])[CH3:21]

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 178520887HCID 178520887, compound

Product 1

HCID 86597779851070-23-0Yield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile (50 ml) solution of (Z)-4,4,4-trifluoro-3-hydroxy-1-(4-trifluoromethyl-phenyl)-but-2-en-1-one (4.7 g, 17 mmol; D. Barrett, P. D. Bentley, T. R. Perrior, Synthetic Commun. 1996, 26, 3401–3406) was added ethyl-3-aminocrotonate (4.27 g, 33 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 2.2 g (5.8 mmol, 35%) of the title compound as yellow crystals.

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-7b2a2b51e622453b9cc629fa565e5ec8
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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