Water → 1-propadienyl-1H-pyrrole-3-carboxaldehyde

HRID 2291924Notes

Reaction equation

HRID 2291924 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[H-].[Na+].[CH2:10](Br)[C:11]#[CH:12].O>O1CCCC1>[CH:10]([N:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1)=[C:11]=[CH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 6403081H-pyrrole-3-carboxaldehyde

Product 1

HCID 450875741-propadienyl-1H-pyrrole-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g of pyrrole-3-carboxaldehyde was dissolved in 25 ml of tetrahydrofuran with stirring at the ambient temperature for 15 minutes and after cooling to 0° to 5° C., 528 mg of sodium hydride as 50% in oil were added with stirring for 10 minutes cold. The temperature was allowed to return to the ambient with stirring for 40 minutes under nitrogen and 1 ml of propargyl bromide was added with stirring for a further 2 hours at 40° to 50° C. Then, the reaction mixture was poured into 15 ml of water, and was extracted with methylene chloride. The extracts were dried and concentrated by distilling off the solvent. The residue was chromatographed over silica and eluted with a mixture of hexane and ethyl acetate (7-3) to obtain 1.166 g of 1-propadienyl-1H-pyrrole-3-carboxaldehyde.

Workup

  1. temperatureafter cooling to 0° to 5° C.
  2. stirringwith stirring for 10 minutes cold
  3. stirringwith stirring for 40 minutes under nitrogen
  4. stirringwith stirring for a further 2 hours at 40° to 50° C
  5. extractionwas extracted with methylene chloride
  6. customThe extracts were dried
  7. concentrationconcentrated
  8. distillationby distilling off the solvent
  9. customThe residue was chromatographed over silica
  10. washeluted with a mixture of hexane and ethyl acetate (7-3)

Sources & evidence

ORD record
ord-d2b062a3b8334a129b7e0f7398381cb1
Source dataset
uspto-grants-1989_01
Patent number
US04798901

Reaction notes

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