Dimethylformamide → 2,5-Dimethyl-1-phenylpyrrole-3-carboxaldehyde

HRID 1642350Notes

Reaction equation

HRID 1642350 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.CN([CH:17]=[O:18])C.P(Cl)(Cl)(Cl)=O.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][C:6]=1[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 665182,5-Dimethyl-1-phenylpyrrole

Product 1

HCID 665152,5-Dimethyl-1-phenylpyrrole-3-carboxaldehydeYield 29.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a well stirred solution of 2,5-dimethyl-1-phenyl-1H-pyrrole (7.65 g, 44.7 mmol) and DMF (3.6 g, 49.2 mmol) in 70 mL of dry toluene, phosphorus oxychloride (6.9 g, 44.7 mmol) was added in small portions. The mixture was heated to 80° C. for 3 hrs. The solution was allowed to cool to room temperature, then 100 mL of saturated aqueous Na2CO3 was added. The aqueous layer was extracted with EtOAc (100 mL×3). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure, the residue was purified by column chromatography (hexane:EtOAc=10:1) to give 2.6 g of 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (29%). MS [M++1]=200, LC-MS: tR=1.96 min.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous layer was extracted with EtOAc (100 mL×3)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (hexane:EtOAc=10:1)

Sources & evidence

ORD record
ord-271540423c924802a38d37ad61840419
Source dataset
uspto-grants-2012_02
Patent number
US08119660B2

Reaction notes

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