Water → 1H-Pyrrole-3-carboxaldehyde,1-(2-propynyl)-(9CI)

HRID 649026Notes

Reaction equation

HRID 649026 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>[CH2:12]([N:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1)[C:11]#[CH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromide2×HCID 24758Sodium hydrideHCID 6403081H-pyrrole-3-carboxaldehyde

Product 1

HCID 136049451H-Pyrrole-3-carboxaldehyde,1-(2-propynyl)-(9CI)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.924 g of pyrrole-3-carboxaldehyde (J. Org. Chem. 1981, Vol. 46, p. 839) dissolved in 45 ml of tetrahydrofuran and 1.488 g of sodium hydride as 50% in oil were admixed and then were stirred for 10 minutes cold, then for 40 minutes at room temperature. After cooling, 2.5 ml of propargyl bromide were added with stirring at 5 C. for 90 minutes. A further 2 ml of propargyl bromide were added with stirring at 5° C. for 1 hour and the mixture was poured into water and extracted with methylene chloride. The solvent was distilled off at atmospheric pressure to obtain 2.868 g of 1-(2-propynyl)-1H-pyrrole-3-carboxaldehyde which was purified by chromatography on silica gel and elution with a 65-35 hexane-ethyl acetate mixture to obtain 2.868 g of the said product.

Workup

  1. waitfor 40 minutes at room temperature
  2. temperatureAfter cooling
  3. stirringwith stirring at 5 C
  4. waitfor 90 minutes
  5. stirringwith stirring at 5° C. for 1 hour
  6. extractionextracted with methylene chloride
  7. distillationThe solvent was distilled off at atmospheric pressure

Sources & evidence

ORD record
ord-c1e93267b96c4bc2a89d829dc643e1a4
Source dataset
uspto-grants-1988_04
Patent number
US04737513

Reaction notes

Loading…