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

HRID 965908

반응식

HRID 965908 반응식
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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 11589Crotyl chlorideHCID 119722-Acetamidophenol

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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):

후처리

  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)

출처 및 근거

ORD 기록
ord-778608e6e13d444fb651b4d9a31d16e0
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951874B2

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