Potassium Carbonate → (Z)-methyl-3-(2-(3,5-difluorophenoxy)acetamido)but-2-enoate

HRID 56244

Reaktionsgleichung

Reaktionsgleichung von HRID 56244
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([F:14])[CH:13]=1.[CH3:16][O:17][C:18](=[O:27])/[CH:19]=[C:20](\[NH:22][C:23](=[O:26])[CH2:24]Br)/[CH3:21]>CC(C)=O>[CH3:16][O:17][C:18](=[O:27])/[CH:19]=[C:20](\[NH:22][C:23](=[O:26])[CH2:24][O:15][C:10]1[CH:9]=[C:8]([F:7])[CH:13]=[C:12]([F:14])[CH:11]=1)/[CH3:21]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 759283,5-DifluorophenolHCID 90023822Methyl 3-(2-bromoacetamido)crotonate

Produkt 1

HCID 90023395(Z)-methyl-3-(2-(3,5-difluorophenoxy)acetamido)but-2-enoateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a suspension of K2CO3 (1.38 g, 10.0 mmol) in acetone (50 mL) were added 3,5-difluorophenol (0.78 g, 6.00 mmol) and (Z)-methyl-3-(2-bromoacetamido)but-2-enoate (1.18 g, 5.00 mmol) and the mixture was refluxed for 5 h. The mixture was cooled to rt and filtered and the filtrate was concentrated in vacuo. To the residue was added DCM (100 mL) and the mixture was washed with water (100 mL×2) and brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1) to give the title compound as a white solid (1.18 g, 83%).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 5 h
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo the residue was added DCM (100 mL)
  5. washthe mixture was washed with water (100 mL×2) and brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-e13f3a43cf4f456b92452b03e1590cab
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434695B2

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