Sulfuric Acid → 2-(4-Propyl-cyclohexanecarbonyl)-malonic acid diethyl ester

HRID 1725181

反応式

HRID 1725181 の反応式
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]([CH:16]1[CH2:21][CH2:20][CH:19]([C:22](Cl)=[O:23])[CH2:18][CH2:17]1)[CH2:14][CH3:15].OS(O)(=O)=O>CCO.C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(Cl)(Cl)(Cl)Cl>[CH2:11]([O:10][C:2](=[O:9])[CH:3]([C:22]([CH:19]1[CH2:20][CH2:21][CH:16]([CH2:13][CH2:14][CH3:15])[CH2:17][CH2:18]1)=[O:23])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

参加物

9

反応物 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224Magnesium2 回HCID 12780024Cyclohexanecarbonyl chloride, 4-propyl-, trans-

生成物 1

HCID 690599802-(4-Propyl-cyclohexanecarbonyl)-malonic acid diethyl ester収率 68.6%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒2 回HCID 1140Toluene溶媒HCID 5943Carbon Tetrachloride溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To 2.5 mL of anhydrous EtOH and 0.25 mL carbon tetrachloride was added 1.2 g (50 mmol) magnesium turnings. 8.0 g (50 mmol) diethyl malonate was dissolved in a mixture of 5 mL anhydrous EtOH and 20 mL anhydrous toluene and added in small portions to the magnesium turnings over the course of 1.5 hr so as to maintain a gentle reflux. The reaction was stirred at room temperature for 1 hr, and then cooled to 0° C. in ice. 4-Propyl-cyclohexanecarbonyl chloride (50 mmol) was added dropwise and the reaction was allowed to warm to room temperature over night. The reaction was then heated to 55° C. for 4 hr with stirring, allowed to cool to ambient temperature, and was poured into a slurry of crushed ice and 10% H2SO4. The solution was diluted with brine and extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated to afford 10.71 g (34.28 mmol) 2-(4-propyl-cyclohexanecarbonyl)-malonic acid diethyl ester as a clear, near colorless oil.

後処理

  1. temperatureto maintain a gentle reflux
  2. temperaturecooled to 0° C. in ice
  3. temperatureto warm to room temperature over night
  4. temperatureThe reaction was then heated to 55° C. for 4 hr
  5. stirringwith stirring
  6. temperatureto cool to ambient temperature
  7. extractionextracted with ethyl acetate
  8. customThe organic layer was separated
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-44c439965f4b4537b0c76da3e33c7e09
出典データセット
uspto-grants-2009_02
特許番号
US07488832B2

関連ノート

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