Citric Acid → Diethyl 2-(4-tolyl)maleate

HRID 2269806노트

반응식

HRID 2269806 반응식
[CH2:1]([O:3][C:4]([CH2:6]P(=O)(OCC)OCC)=[O:5])[CH3:2].[H-].[Na+].[C:17]1([CH3:30])[CH:22]=[CH:21][C:20]([C:23](=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:17]1([CH3:30])[CH:18]=[CH:19][C:20](/[C:23](=[CH:6]/[C:4]([O:3][CH2:1][CH3:2])=[O:5])/[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][CH:22]=1

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 2736443Ethyl 2-(4-methylphenyl)-2-oxoacetate

생성물 1

HCID 18348039Diethyl 2-(4-tolyl)maleate수율 92.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of diethyl ethoxycarbonylmethylphosphonate (3.3 g) in anhydrous tetrahydrofuran (20 ml) is added dropwise to a suspension of sodium hydride (60%, oily) (676 mg) in anhydrous tetrahydrofuran (30 ml) under a nitrogen atmosphere and ice cooling, and further a solution of ethyl 4-tolylglyoxylate (2.96 g) in anhydrous tetrahydrofuran (22 ml) is added dropwise thereto. The mixture is stirred at room temperature for 30 minutes, a 10% aqueous citric acid solution is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 3.57 g (88%) of diethyl 2-(4-tolyl)maleate.

후처리

  1. extractionthe whole is extracted with ether
  2. washThe organic layer is washed with water and saturated brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a34f7d74637d464c9090e1aba6a66d1b
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329547B1

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