Reaktion #40891

Reaktionsgleichung

ethyl acetate

triethylamine

2,4-dichlorobenzoyl chloride

→

ethyl [3-(2,4-dichlorobenzoyl)-2-oxocyclohexyl]acetate

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 16 h
2. 2
   Temperaturto cool
3. 3
   Waschenwashed with saturated sodium bicarbonate
4. 4
   TrocknenThe organics were dried over sodium sulfate
5. 5
   Sonstigepurified by column chromatography

Vorschrift

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).

Quelle