Reacción #40891

Ecuación de reacción

ethyl acetate

triethylamine

2,4-dichlorobenzoyl chloride

→

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

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 16 h
2. 2
   Temperaturato cool
3. 3
   Lavadowashed with saturated sodium bicarbonate
4. 4
   SecadoThe organics were dried over sodium sulfate
5. 5
   Otropurified by column chromatography

Procedimiento

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).

Fuente