Acetic Acid → Ethyl 3-anilinobut-2-enoate

HRID 1410873

Reaktionsgleichung

Reaktionsgleichung von HRID 1410873
[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]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 6115AnilineHCID 8868Ethyl Acetoacetate

Produkt 1

HCID 94928Ethyl 3-anilinobut-2-enoateAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-fe19160a05714c19908448f3a1622dd8
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921389B2

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