Potassium Carbonate → N-{2-[(E)-1-Propenyloxy)phenyl}acetamide

HRID 965908

Reaktionsgleichung

Reaktionsgleichung von HRID 965908
Cl[CH2:2][CH:3]=[CH:4]C.[C:6]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])(=[O:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:2](/[O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:6](=[O:8])[CH3:7])=[CH:3]\[CH3:4]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11589Crotyl chlorideHCID 119722-Acetamidophenol

Produkt 1

HCID 22313764N-{2-[(E)-1-Propenyloxy)phenyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A heterogenic mixture of commercially available 1-chloro-2-butene (Aldrich, predominantly trans) (453 mg, 0.49 mL, 5.00 mmol), 2-acetamidophenol (756 mg, 5.00 mmol) and potassium carbonate (691 mg, 5.00 mmol) in aceton (10 ml) was heated to reflux over night. After evaporation of the solvent the residue was taken up by ethylacetate and water. Washing of the organic phase with water, 5-proz. sodium hyroxide and brine and evaporation of the solvent afforded the crude which was purified by flash chromatography on silica gel (heptane/EtOAc=3:2). Yield: 732 mg (71%) of a brownish yellow solid. Trans:cis=81:19 (ratio determined by 1H-NMR; 400 MHz, CDCl3):

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux over night
  3. customAfter evaporation of the solvent the residue
  4. washWashing of the organic phase with water
  5. customsodium hyroxide and brine and evaporation of the solvent
  6. customafforded the crude which
  7. customwas purified by flash chromatography on silica gel (heptane/EtOAc=3:2)

Quellen und Nachweise

ORD-Eintrag
ord-778608e6e13d444fb651b4d9a31d16e0
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951874B2

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