Diethyl Malonate → Diethyl (3-fluoro-2-pyridyl)malonate

HRID 1907687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907687
F[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:8][C:7]1[C:2]([CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([O:17][CH2:18][CH3:19])=[O:16])=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 27831762,3-Difluoropyridine

Produkt 1

HCID 57950221Diethyl (3-fluoro-2-pyridyl)malonateAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3.95 g of 2,3-difluoropyridine, 13.2 g of diethyl malonate, 38 ml of dimethyl sulfoxide and 26.85 g of cesium carbonate was stirred for 3 hours at 100° C. under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, then, to this was added ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine twice, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. 12.18 g of the resultant residue was subjected to silica gel column chromatography, to obtain 6.38 g of diethyl (3-fluoro-2-pyridyl)malonate.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cc1c08c2be1c40b89d03118e493c9979
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598176B2

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