Dimethyl malonate → Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate

HRID 24441

Reaktionsgleichung

Reaktionsgleichung von HRID 24441
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Cl[C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24]>CS(C)=O>[CH3:22][O:21][C:19]([C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:23]([O-:25])=[O:24])[C:13]=1[CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[O:20]

Komponenten

5

Edukt 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Produkt 1

HCID 54355276Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Dimethyl malonate (6.0 ml) was added to an ice-cold suspension of sodium hydride (2.1 g) in dimethylsulfoxide (15 ml). The reaction mixture was heated to 100° C., stirred for 1 hour and then cooled to room temperature. 2-Chloro-3-methoxycarbonylnitrobenzene (2.15 g) was added in one portion and the mixture was stirred at 100° C. for 1.5 hour. The reaction mixture was then cooled to room temperature and poured into ice water, acidified to pH 5, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give 3.0 g of the dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. stirringthe mixture was stirred at 100° C. for 1.5 hour
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ccbe698d28b142d09fe9146b2e53ddaf
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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