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

HRID 1096970Notes

Reaction equation

HRID 1096970 reaction equation
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[CH:11]1([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH2:13][CH2:12]1.[OH-].[Na+]>>[CH:11]1([N:14]2[CH:18]=[CH:17][CH:16]=[C:15]2[CH:9]=[O:10])[CH2:13][CH2:12]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

In a 500-ml egg plant-type flask, POCl3 (44.46 mL, 0.48 mol) was dropwise added to a DMF (37 mL, 0.48 mol) solution of 1-cyclopropyl-1H-pyrrole (46.46 g, 0.43 mol) with cooling with ice, and then stirred overnight at room temperature. The reaction mixture was poured into 5 N sodium hydroxide solution (336 mL) with cooling with ice, and the reaction solution was made basic with 5 N sodium hydroxide solution added thereto. The mixture solution was extracted with dichloromethane, dried with sodium sulfate, filtered, concentrated, and purified through silica gel column chromatography (Biotage [SiO2, 75+M]) with a hexane/ethyl acetate developer system to obtain the title compound as a colorless oil.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice
  3. additionadded
  4. extractionThe mixture solution was extracted with dichloromethane
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified through silica gel column chromatography (Biotage [SiO2, 75+M]) with a hexane/ethyl acetate developer system

Sources & evidence

ORD record
ord-07f3e329ea034596b2db6745ceecca08
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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