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

HRID 496206

Reaktionsgleichung

Reaktionsgleichung von HRID 496206
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-1a3cc38589a44682acd1a2e0f5c6aaf2
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943188B2

Verknüpfte Notizen

Wird geladen…