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

HRID 584626Notes

Reaction equation

HRID 584626 reaction equation
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]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11589Crotyl chlorideHCID 119722-Acetamidophenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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):

Workup

  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)

Sources & evidence

ORD record
ord-75b0f2dddd3e4fc6b5c3338f5f7204f4
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

Loading…