1,2-Dichloroethane → 1-phenyl-1H-pyrrole-2-carbaldehyde

HRID 880454

反応式

HRID 880454 の反応式
P(Cl)(Cl)(Cl)=[O:2].[C:6]1([N:12]2C=[CH:15][CH:14]=[CH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:17](Cl)[CH2:18]Cl>>[C:6]1([N:12]2[CH:13]=[CH:14][CH:15]=[C:17]2[CH:18]=[O:2])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

4

反応物 3

HCID 111,2-DichloroethaneHCID 124801-PhenylpyrroleHCID 24813Phosphorus oxychloride

生成物 1

HCID 9347291-phenyl-1H-pyrrole-2-carbaldehyde収率 59%

実験手順

Phosphorus oxychloride (0.7 mL, 7.68 mmol) was added slowly to ice-cold dimethylformamide (0.6 mL, 7.68 mmol). The mixture was warmed to room temperature and stirred for 15 min. A solution of 1-phenylpyrrole (1.0 g, 6.98 mmol) in ethylene dichloride (5 mL) was added and the reaction mixture heated at reflux for 1 h. The mixture was cooled to 10° C. and quenched into 10% sodium acetate solution (20 mL). The organic layer was separated and the aqueous phase was extracted with ether. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under in vacuo to give a crude residue. Purification by column chromatography over silica gel (60-120 mesh) using 2% ethyl acetate in petroleum ether as eluent gave 1-phenylpyrrole-2-carbaldehyde (700 mg, 59%) as a colourless oil.

後処理

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1 h
  3. temperatureThe mixture was cooled to 10° C.
  4. customquenched into 10% sodium acetate solution (20 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous phase was extracted with ether
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under in vacuo
  11. customto give a crude residue
  12. customPurification by column chromatography over silica gel (60-120 mesh)

出典と根拠

ORDレコード
ord-66e267d473094e30bcbbd712a3c1ef4d
出典データセット
uspto-grants-2015_03
特許番号
US08993574B2

関連ノート

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