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

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

反応物 3

HCID 111,2-Dichloroethane

HCID 124801-Phenylpyrrole

HCID 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.