Water → Ethyl 1,4-dimethyl-1H-pyrrole-2-acetate

HRID 894471Notes

Reaction equation

HRID 894471 reaction equation
S([O:7][CH2:8][CH3:9])(OCC)(=O)=O.[CH3:10][N:11]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]1[CH2:17][C:18](O)=[O:19].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:10][N:11]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]1[CH2:17][C:18]([O:7][CH2:8][CH3:9])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 3018854(1,4-Dimethyl-1H-pyrrol-2-yl)acetic acid

Product 1

HCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 5.48 ml (0.042 mol) sample of diethyl sulfate was added to a suspension of 6.12 g (0.040) of 1,4-dimethylpyrrole-2-acetic acid and 16.6 g (0.12 mol) of potassium carbonate in 50 ml of DMSO. The mixture was stirred for 6 hours at room temperature. It was poured into water and extracted with ether. The ether extract was washed with brine, dried (MgSO4) and the solvent was evaporated in vacuo. The oily residue was distilled to give 6.0 g of ethyl 1,4-dimethylpyrrole-2-acetate, bp 68° at 0.005 Torr as a colorless oil.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated in vacuo
  6. distillationThe oily residue was distilled

Sources & evidence

ORD record
ord-b70b369fdc324908b44b6fe4072c595a
Source dataset
uspto-grants-1981_08
Patent number
US04284562

Reaction notes

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