Diethyl Malonate → 2-(3,5-Difluoro-pyridin-2-yl)-malonic acid diethyl ester

HRID 82285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82285
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.[C:10]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.C(OCC)(=O)C>[CH2:15]([O:14][C:12](=[O:13])[CH:11]([C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1)[C:10]([O:18][CH2:19][CH3:20])=[O:17])[CH3:16]

Komponenten

6

Edukt 3

HCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 27832872,3,5-Trifluoropyridine

Produkt 1

HCID 708176062-(3,5-Difluoro-pyridin-2-yl)-malonic acid diethyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a stirred solution of 2,3,5-trifluoro-pyridine (2 g, 15.02 mmol) in dimethyl sulfoxide (20 mL) was added diethyl malonate (4.60 g, 28.72 mmol). Then cesium carbonate (9.35 g, 28.72 mmol) was added and the reaction mixture was heated to 110° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 mL). The organic layer was washed with water (2×25 mL), brine (25 mL), dried over sodium sulphate and evaporated in vacuo to afford the title compound as oil in 85% yield, 3.5 g.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with water (2×25 mL), brine (25 mL)
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d7a2bddfc36c49a9939cb41f30b06704
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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