Acetic Anhydride → 4-(4-(trifluoromethyl)benzyloxy)pyridin-2(1H)-one

HRID 2202842

Reaktionsgleichung

Reaktionsgleichung von HRID 2202842
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(OC(=O)C)(=[O:22])C>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][NH:12][C:11](=[O:22])[CH:10]=2)=[CH:5][CH:4]=1

Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 686576494-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxide

Produkt 1

HCID 579504804-(4-(trifluoromethyl)benzyloxy)pyridin-2(1H)-one

Versuchsvorschrift

A solution of 4-((4-(trifluoromethyl)benzyl)oxy)pyridine 1-oxide (350 mg) in acetic anhydride (6 ml) was heated under reflux for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was diluted with MeOH (10 ml) and 2 M NaOH (10 ml), and heated at reflux for 1 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with water and extracted with DCM. The DCM layer was concentrated in vacuo and purified by silica gel column chromatography (MeOH/DCM) to give the title compound (110 mg) as an off-white solid.

Aufarbeitung

  1. temperatureunder reflux for 4 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with MeOH (10 ml) and 2 M NaOH (10 ml)
  4. temperatureheated
  5. temperatureat reflux for 1 h
  6. temperatureThe reaction mixture was cooled to room temperature
  7. concentrationconcentrated in vacuo
  8. additionThe residue was diluted with water
  9. extractionextracted with DCM
  10. concentrationThe DCM layer was concentrated in vacuo
  11. custompurified by silica gel column chromatography (MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-5ade6a1d9ba7468caf5ad965a11d205c
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365540B2

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