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

Reaction equation

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]

Participants

Procedure

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).