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

HRID 12613

反応式

HRID 12613 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e96109b552dd4f269eee287f5bebff85
出典データセット
uspto-grants-2010_06
特許番号
US07728022B2

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