p-Toluenesulfonic acid monohydrate → 3-methoxy-1H-Pyrrole-2,5-dione

HRID 928204Notes

Reaction equation

HRID 928204 reaction equation
[CH3:1][O:2][C:3]1(OC)[CH2:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][C:6](=[O:8])[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 14567650HCID 14567650, compound

Product 1

HCID 116726673-methoxy-1H-Pyrrole-2,5-dioneYield 70.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,3-dimethoxypyrrolidine-2,5-dione (12.3 g, 77 mmol) in toluene (500 mL) was added TsOH·water (1.46 g, 7.7 mmol). A Dean Stark Trap was attached and the reaction mixture was refluxed overnight. TLC (petroleum ether/EtOAc=1/1) showed the reaction was complete. The mixture was concentrated and purified by column chromatography (from petroleum ether/EtOAc=2/1 to petroleum ether/EtOAc=1/1) to afford 3-methoxy-1H-pyrrole-2,5-dione (6.9 g, 70% yield) as an orange solid.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. concentrationThe mixture was concentrated
  3. custompurified by column chromatography (from petroleum ether/EtOAc=2/1 to petroleum ether/EtOAc=1/1)

Sources & evidence

ORD record
ord-aa6b13fe041443d0a6e119d9563d9bed
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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