Hydrochloric Acid → HCID 10960547, Verbindung

HRID 1873227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873227
Cl[C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[C:29]([O:35][CH3:36])(=[O:34])[CH2:30][C:31]([CH3:33])=[O:32].Cl>CS(C)=O>[C:31]([CH:30]([C:29]([O:35][CH3:36])=[O:34])[C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])(=[O:32])[CH3:33]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 11430Potassium CarbonateHCID 12854241Propanedioic acid, 2-(3-chloro-4-nitrophenyl)-2-methyl-, 1,3-diethyl ester

Produkt 1

HCID 10960547HCID 10960547, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of diethyl 2-(3-chloro-4-nitrophenyl)-2-methylmalonate (1.0 g, 3.03 mmol.) in dimethyl sulfoxide (DMSO, 3mL) were added potassium carbonate (1.25 g, 9.09 mmol.) and methyl acetoacetate (0.99 mL, 9.0 mmol.). The resulting mixture was stirred at 70° C. for 6 hours. The reaction mixture was cooled to room temperature, neutralized with diluted hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate portion was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The dried portion was concentrated to leave a residue. The residue was purified by silica gel column chromatography (Wako Gel C-330, available from Wako Jyunyaku Industry Co., Ltd., toluene/ethyl acetate=100/4, v/v), to give 0.64 g (yield: 52%) of the desired compound as a yellow oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate portion was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe dried portion was concentrated
  6. customto leave a residue
  7. customThe residue was purified by silica gel column chromatography (Wako Gel C-330, available from Wako Jyunyaku Industry Co., Ltd., toluene/ethyl acetate=100/4, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-cb7dc4cca6a847d4a69e9acb83382314
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06111115

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