Dimethylformamide → 1-cyclopropyl-1H-pyrrole-2-carbaldehyde

HRID 420137Notes

Reaction equation

HRID 420137 reaction equation
O=P(Cl)(Cl)Cl.[CH:6]1([N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)[CH2:8][CH2:7]1.CN([CH:17]=[O:18])C>>[CH:6]1([N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[CH:17]=[O:18])[CH2:8][CH2:7]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 189896721-Cyclopropyl-1H-pyrrole

Product 1

HCID 434769981-cyclopropyl-1H-pyrrole-2-carbaldehyde

Procedure

44.46 ml of POCl3 was added to a stirred solution of 1-cyclopropyl-1H-pyrrole (46.46 g) in 37 ml of DMF with cooling with ice, then the mixture was stirred at room temperature overnight. The mixture was poured into 336 ml of 5N NaOHaq with cooling with ice, and the mixture was made basic with an additional 5N NaOHaq. The mixture was extracted with CH2Cl2 and the organic extract was dried over Na2SO4, concentrated, and the residue was purified on SiO2 column chromatography (n-hexane-EtOAc system) to give 38.91 g of 1-cyclopropyl-1H-pyrrol-2-carbaldehyde as a colorless oil.

Workup

  1. temperaturewith cooling with ice
  2. additionThe mixture was poured into 336 ml of 5N NaOHaq
  3. temperaturewith cooling with ice
  4. extractionThe mixture was extracted with CH2Cl2
  5. extractionthe organic extract
  6. dry with materialwas dried over Na2SO4
  7. concentrationconcentrated
  8. customthe residue was purified on SiO2 column chromatography (n-hexane-EtOAc system)

Sources & evidence

ORD record
ord-86f6625a749f44029d6544488f31e585
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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