Reaction equation
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]=1Participants
Procedure
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.
Workup
- temperaturethe reaction mixture heated
- temperatureat reflux for 1 h
- temperatureThe mixture was cooled to 10° C.
- customquenched into 10% sodium acetate solution (20 mL)
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with ether
- washThe combined organic layers were washed with water, brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under in vacuo
- customto give a crude residue
- customPurification by column chromatography over silica gel (60-120 mesh)
Sources & evidence
- ORD record
- ord-66e267d473094e30bcbbd712a3c1ef4d
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993574B2
Linked notes
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