Diethyl Malonate → HCID 67979448, Verbindung

HRID 539288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539288
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Br:14][C:15]1[CH:16]=[C:17]([Cl:22])[C:18](Cl)=[N:19][CH:20]=1>CN(C=O)C>[Br:14][C:15]1[CH:16]=[C:17]([Cl:22])[C:18]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[N:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 127477605-Bromo-2,3-dichloropyridine

Produkt 1

HCID 67979448HCID 67979448, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Diethyl malonate (0.87 mL, 5.7 mmol) was added dropwise to a suspension of NaH (55% in mineral oil, 0.27 g, 6.2 mmol) in DMF (6 mL) at 0° C. The ice-bath was removed and the mixture was stirred under N2 at r.t. for 20 min. 5-Bromo-2,3-dichloropyridine (1.0 g, 4.4 mmol) was added, and the mixture was stirred at 120° C. overnight. The mixture was allowed to cool and was then partitioned between water containing NaCl and EtOAc. The organic phase was dried (MgSO4) and evaporated to give a crude product which was purified by flash chromatography (25 g SiO2, heptane/EtOAc gradient) affording the title compound (0.8 g, 2 mmol, 52% yield) containing a residue of unreacted malonic ester. MS (ES+) m/z 350 [M+H]+. A part of this material was used as such in the subsequent step.

Aufarbeitung

  1. customThe ice-bath was removed
  2. stirringthe mixture was stirred at 120° C. overnight
  3. temperatureto cool
  4. customwas then partitioned between water
  5. additioncontaining NaCl and EtOAc
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customevaporated
  8. customto give a crude product which
  9. customwas purified by flash chromatography (25 g SiO2, heptane/EtOAc gradient)

Quellen und Nachweise

ORD-Eintrag
ord-bd6a45472fca4423a646b7ce12a43abf
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865911B2

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