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

HRID 38489Notes

Reaction equation

HRID 38489 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.[OH-].[Na+].CN([CH:19]=[O:20])C>>[CH:6]1([N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[CH:19]=[O:20])[CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 189896721-Cyclopropyl-1H-pyrrole

Product 1

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

Procedure

POCl3 (44.5 ml) was added to a stirred solution of 1-cyclopropyl-1H-pyrrole (46.5 g) in DMF (37 ml) at 0° C., then the mixture was stirred at room temperature overnight. The mixture was poured into aqueous 5N NaOH (336 ml) at 0° C., and the mixture was made basic with an additional aqueous 5N NaOH. The mixture was extracted with CH2Cl2 and the organic extract was dried over Na2SO4, concentrated, and the residue was purified on silicagel column chromatography (hexane/EtOAc) to give intended compound as colorless oil.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. extractionthe organic extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified on silicagel column chromatography (hexane/EtOAc)
  6. customto give

Sources & evidence

ORD record
ord-f356231ba4b8489a8306a461e698bc22
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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