Acetic Acid → Ethyl 3-anilinobut-2-enoate

HRID 919867

Reaction equation

HRID 919867 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6](=O)[CH3:7])[CH3:2].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C>CCO>[CH2:1]([O:3][C:4](=[O:9])[CH:5]=[C:6]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6115AnilineHCID 8868Ethyl Acetoacetate

Product 1

HCID 94928Ethyl 3-anilinobut-2-enoateYield 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-oxo-butyric acid ethyl ester (7 mL, 53.7 mmol), aniline (5 g, 53.7 mmol), acetic acid (0.060 mL) and 4 Å molecular sieves (5 g) in EtOH (20 mL) was refluxed for 5 h. After cooling to r.t., the mixture was filtered. EtOAc was added to rinse the solids, and the filtrate was concentrated to give a reddish oil, which was purified by silica gel chromatography (0-10% EtOAc/hexanes) to give 7 g of the title compound as a pale yellow oil. 1H NMR (CDCl3, 200 MHz): δ=10.38 (br s, 1H), 7.00-7.40 (m, 5H), 4.69 (s, 1H), 4.15 (q, 2H, J=7.0 Hz), 2.00 (s, 3H), 1.29 (t, 3H, J=7.0 Hz).

Workup

  1. temperaturewas refluxed for 5 h
  2. filtrationthe mixture was filtered
  3. additionEtOAc was added
  4. washto rinse the solids
  5. concentrationthe filtrate was concentrated
  6. customto give a reddish oil, which
  7. customwas purified by silica gel chromatography (0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9681e989c3d549e0a8872c14392b55ed
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Linked notes

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