Water → 1-Tosylpyrrole

HRID 1883170Notes

Reaction equation

HRID 1883170 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.O>C1COCC1>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([N:3]2[CH:7]=[CH:6][CH:5]=[CH:4]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8027PyrroleHCID 24758Sodium hydride

Product 1

HCID 6400871-TosylpyrroleYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 60% NaH (3.13 g) in THF (20 mL) was added dropwise a solution of pyrrole (5.00 g) in THF (20 mL). The mixture was stirred for 30 minutes, and thereto was added a solution of p-toluene sulfonylchloride (14.2 g) in THF (20 mL), and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the organic layer was separated, dried, filtered, and concentrated. The residue was recrystallized from a mixed solvent of methanol and water (each 35 mL), and the resulting crystals were collected by filtration, and dried to give 1-p-toluenesulfonyl-1H-pyrrole (16.3 g, 99%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customthe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized from a mixed solvent of methanol and water (each 35 mL), and the resulting crystals
  7. filtrationwere collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-778d57635ffa4a07ba74ab4e07437f7a
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

Loading…