Water → 1-(4-methylbenzenesulfonyl)-1H-pyrrole-3-carboxylic acid

HRID 1748650ノート

反応式

HRID 1748650 の反応式
C([O:5][C:6]([C:8]1[CH:12]=[CH:11][NH:10][CH:9]=1)=[O:7])(C)(C)C.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>O1CCCC1.[H-].[Na+]>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:10]2[CH:11]=[CH:12][C:8]([C:6]([OH:5])=[O:7])=[CH:9]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 11171190tert-butyl 1H-pyrrole-3-carboxylate

生成物 1

HCID 27246931-(4-methylbenzenesulfonyl)-1H-pyrrole-3-carboxylic acid収率 74.2%

試薬・触媒・溶媒 2

HCID 24758Sodium hydride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60%; 1.02 mg) was added at 0° C. to a solution of 1H-pyrrole-3-carboxylic acid tert-butyl ester (3.57 g) in tetrahydrofuran (71 ml), stirred at room temperature, then p-toluenesulfonic acid chloride (4.47 g) the mixture was stirred all night and all day. Water was added to the reaction solution, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The organic solution was concentrated in vacuo, dichloromethane (30 ml) and trifluoroacetic acid (15 ml) were added to the resulting residue and stirred at room temperature for four hours. The solvent was evaporated, water was added to the resulting residue and the precipitated solid was washed with water to give 1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3-carboxylic acid (4.2 g) as a pale yellow solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic solution was concentrated in vacuo, dichloromethane (30 ml) and trifluoroacetic acid (15 ml)
  5. additionwere added to the resulting residue
  6. stirringstirred at room temperature for four hours
  7. customThe solvent was evaporated
  8. additionwater was added to the resulting residue
  9. washthe precipitated solid was washed with water

出典と根拠

ORDレコード
ord-9f6fd9551b4444a4bb6b0980a041c598
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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