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

HRID 1242453Notes

Reaction equation

HRID 1242453 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-4e54f5c1782d4437926cdae7e522f05b
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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