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

HRID 2269806ノート

反応式

HRID 2269806 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 18348039Diethyl 2-(4-tolyl)maleate収率 92.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a34f7d74637d464c9090e1aba6a66d1b
出典データセット
uspto-grants-2001_12
特許番号
US06329547B1

反応ノート

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