Benzoyl chloride → 1-Benzoyl-3-formyl-pyrrole

HRID 2291929Notes

Reaction equation

HRID 2291929 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][NH:5][CH:4]=1)=[O:2].[H-].[Na+].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.O>[C:10]([N:5]1[CH:6]=[CH:7][C:3]([CH:1]=[O:2])=[CH:4]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 6403081H-pyrrole-3-carboxaldehyde

Product 1

HCID 212785171-Benzoyl-3-formyl-pyrrole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

500 mg of 3-formyl-pyrrole were dissolved in 10 ml of tetrahydrofuran and then, at +20° C., 227 mg of sodium hydride dispersed at 55% in vaseline oil were added all at once. Gas evolved and after stirring for 15 minutes, a solution of 0.58 ml of benzoyl chloride in 2 ml of tetrahydrofuran was introduced dropwise at +5° C. The mixture was stirred for 2 hours at 20° C. and diluted with water. Extracting with ether, concentrating to dryness by distillation under reduced pressure and chromatographing the residue over silica and eluting with a mixture of hexane and ethyl acetate (7-3) yielded 558 mg of 1-benzoyl-3-formyl-pyrrole.

Workup

  1. additionwere added all at once
  2. stirringThe mixture was stirred for 2 hours at 20° C.
  3. extractionExtracting with ether
  4. concentrationconcentrating to dryness by distillation under reduced pressure and chromatographing the residue over silica
  5. washeluting with a mixture of hexane and ethyl acetate (7-3)

Sources & evidence

ORD record
ord-635ac22f73f948ffb14caa23dd488f61
Source dataset
uspto-grants-1989_01
Patent number
US04798901

Reaction notes

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