Water → 3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one

HRID 85195

Reaktionsgleichung

Reaktionsgleichung von HRID 85195
CC(C)([O-])C.[K+].[Si:7]([O:24][CH2:25][C:26]1[C:27](=[O:32])[NH:28][CH:29]=[CH:30][CH:31]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:33][C:34]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[CH:36][C:35]=1F.O>CN(C=O)C>[Si:7]([O:24][CH2:25][C:26]1[C:27](=[O:32])[N:28]([C:35]2[CH:36]=[CH:37][C:38]([N+:40]([O-:42])=[O:41])=[CH:39][C:34]=2[Cl:33])[CH:29]=[CH:30][CH:31]=1)([C:20]([CH3:23])([CH3:21])[CH3:22])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 23665647Potassium tert-butoxideHCID 594101563-({[tert-Butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

Produkt 1

HCID 594101863-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

At 0° C., 0.500 g (4.46 mmol) of potassium tert-butoxide is added to 1.08 g (2.97 mmol) of the compound from Example 3A in 21 ml of DMF, and the mixture is stirred at room temperature for 30 min. 0.571 g (3.27 mmol) of 2-chloro-1-fluoro-4-nitrobenzene is added, and the mixture is stirred at RT. After 4.5 h, 200 ml of water are added, and the mixture is then extracted three times with ethyl acetate. The combined organic phases are washed with water and then dried over sodium sulphate. After filtration, the solvents are removed under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1). This gives 872 mg (56% of theory) of the desired compound.

Aufarbeitung

  1. stirringthe mixture is stirred at RT
  2. waitAfter 4.5 h
  3. extractionthe mixture is then extracted three times with ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration
  7. customthe solvents are removed under reduced pressure
  8. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-445897fbd85c41d594077132b150d2ba
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846934B2

Verknüpfte Notizen

Wird geladen…