Water → Deschloroclofibrate

HRID 1429449

Reaktionsgleichung

Reaktionsgleichung von HRID 1429449
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].C([O-])([O-])=O.[Cs+].[Cs+].O>CC#N>[CH3:15][C:9]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 996PhenolHCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Produkt 1

HCID 86476DeschloroclofibrateAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of phenol (2 g, 21.25 mmol) in CH3CN (50 mL) was added ethyl 2-bromo-2-methylpropanoate (5 g, 25.5 mmol) and Cs2CO3 (20 g, 63.75 mmol) at 25° C. The mixture was heated at reflux for 16 h then water (100 mL) added and extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (2.1 g, 47.7%) as colorless oil which was used in next step without further purification.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe organic layer was washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-282f71e9c33841f5a7cfa6acbbd485ac
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940726B2

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