Hydrochloric Acid → Ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate

HRID 732113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732113
[H-].[Na+].[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)=[O:5].[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>CN(C=O)C.CC(=O)OCC>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[O:19])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)=[O:5])[CH3:18]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 149331-(3-Chlorophenyl)ethanoneHCID 24758Sodium hydride

Produkt 1

HCID 11054223Ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoateAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Sodium hydride (60% oil dispersion, 1.24 g, 31.1 mmol) was added in portions to a solution of 3-chloroacetophenone (4.0 g, 25.9 mmol) and diethyl oxalate (4.54 g, 31.1 mmol) in DMF (32 mL) at 0° C. The mixture was stirred at r.t for 1 h and was then heated at 80° C. for 0.5 h. After cooling, the mixture was treated with 3N HCl and then diluted with EA. The organic layer was washed with water and saturated brine, dried (Na2SO4), filtered and concentrated. The resulting residue was then purified by column chromatography using 0-10% EA in hex to afford the title compound (4.43g, 67%). 1H NMR: 15.12 (br s, 1H), 7.98 (s, 1H), 7.88 (d, 1H), 7.58 (d, 1H), 7.47 (t, 1H), 7.05 (s, 1H), 4.39 (m, 2H), 1.41 (m, 3H).

Aufarbeitung

  1. temperatureAfter cooling
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was then purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9cd959022b5f4bff87b4af8b17ed4a0e
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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