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Sodium hydride → Propanedioic acid, 2-(5-chloro-2,4-dinitrophenyl)-, 1-(1,1-dimethylethyl) 3-ethyl ester

HRID 1773532
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773532
[H-].[Na+].[C:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:16][C:17]1[CH:22]=[C:21](Cl)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28]>CN1CCCC1=O>[CH2:8]([O:7][C:5](=[O:6])[CH:4]([C:21]1[CH:22]=[C:17]([Cl:16])[C:18]([N+:27]([O-:29])=[O:28])=[CH:19][C:20]=1[N+:24]([O-:26])=[O:25])[C:3]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH3:9]
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 772861,3-Dichloro-4,6-dinitrobenzeneHCID 96345tert-Butyl ethyl malonate

Produkt 1

HCID 86661368Propanedioic acid, 2-(5-chloro-2,4-dinitrophenyl)-, 1-(1,1-dimethylethyl) 3-ethyl esterAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidone
Lösungsmittel

Versuchsvorschrift

Sodium hydride (60% suspension in mineral oil, 1.60 mmol) was added to a mixture of tert-butyl ethyl malonate (300 mg) in 1-methyl-2-pyrrolidinone (3 mL) and was followed by 1,5-dichloro-2,4-dinitrobenzene (0.45 g). The reaction mixture was stirred for 15 minutes and was then quenched by addition of a diluted aqueous solution of hydrochloric acid. The resulting mixture was extracted with ethyl acetate; the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (EtOAc/hexane, 5/95 to 15/85) to give 0.4 g of 2-(5-chloro-2,4-dinitro-phenyl)-malonic acid tert-butyl ester ethyl ester.

Aufarbeitung

  1. customwas then quenched by addition of a diluted aqueous solution of hydrochloric acid
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (EtOAc/hexane, 5/95 to 15/85)

Quellen und Nachweise

ORD-Eintrag
ord-66d4b6856f20489aba57d74b05357619
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09255110B2

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