Triethylamine → Ethyl [3-(2,4-dichlorobenzoyl)-2-oxocyclohexyl]acetate

HRID 12613

Reaktionsgleichung

Reaktionsgleichung von HRID 12613
C(N([CH2:6][CH3:7])CC)C.[Cl:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11](Cl)=[O:12].[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20]>O1CCOCC1>[Cl:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11]([CH:7]1[CH2:6][CH2:17][CH2:9][CH:10]([CH2:20][C:19]([O:22][CH2:23][CH3:24])=[O:21])[C:11]1=[O:12])=[O:12]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 666452,4-Dichlorobenzoyl chloride

Produkt 1

HCID 86615521Ethyl [3-(2,4-dichlorobenzoyl)-2-oxocyclohexyl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Intermediate 2 (2 g, 8.44 mmol) was dissolved in dioxane (50 ml) and triethylamine (1.18 ml, 8.44 mmol) and 2,4-dichlorobenzoyl chloride (1.76 g, 844 mmol) added. The reaction mixture was stirred at reflux for 16 h. The mixture was then allowed to cool and diluted with ethyl acetate and washed with saturated sodium bicarbonate and then brine. The organics were dried over sodium sulfate and purified by column chromatography to give the desired ethyl [3-(2,4-dichlorobenzoyl)-2-oxocyclohexyl]acetate (220 mg) as a colourless oil. 1H NMR δ (ppm)(CDCl3): 7.36 (1H, d, J=2.0 Hz), 7.23, (1 H, dd, J=8.3, 2.0 Hz), 7.12 (1 H, d, J=8.3 Hz), 4.13-4.07 (2 H, m), 2.93-2.84 (1 H, m), 2.78 (1 H, dd, J=16.1, 5.9 Hz), 2.45 (1 H, dd, J=16.1, 8.3 Hz), 2.11-1.84 (4 H, m), 1.70-1.62 (1 H, m), 1.51-1.40 (2 H, m), 1.20 (3 H, t, J=7.0 Hz).

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. temperatureto cool
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialThe organics were dried over sodium sulfate
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e96109b552dd4f269eee287f5bebff85
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728022B2

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