Dimethylacetamide → 1-(5-Chloropyridin-2-yl)ethan-1-one

HRID 1437268

Reaktionsgleichung

Reaktionsgleichung von HRID 1437268
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.CN(C)[C:16](=[O:18])[CH3:17]>CCCCCC.C(OCC)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:16](=[O:18])[CH3:17])=[N:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 31374DimethylacetamideHCID 8170982-Bromo-5-chloropyridineHCID 178418339Butyllithium

Produkt 1

HCID 101541661-(5-Chloropyridin-2-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Under cooling at −78° C., 1.56M n-butyllithium in hexane (27 mL) was added dropwise to 2-bromo-5-chloropyridine (6.8 g) in diethyl ether (45 mL), and then N,N-dimethylacetamide (5 mL) was added dropwise thereto, followed by stirring for 30 minutes. The reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give 1-(5-chloro-2-pyridyl)ethanone as a solid (3.26 g, 59%).

Aufarbeitung

  1. customThe reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. filtrationfollowed by filtration
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-54878bc4476e4bd69c7dbfe10a028619
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622471B2

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