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

HRID 12613

반응식

HRID 12613 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e96109b552dd4f269eee287f5bebff85
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728022B2

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