Diethyl Ether → Methyl 5-chloro-1-methyl-1H-pyrrole-3-carboxylate

HRID 1981027Notes

Reaction equation

HRID 1981027 reaction equation
[Cl:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[CH:3]=1.[CH3:11]COCC.[H-].[Na+].S(OC)(OC)(=O)=O>O>[CH3:11][N:6]1[C:2]([Cl:1])=[CH:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6497Dimethyl SulfateHCID 24758Sodium hydride2×HCID 12897088HCID 12897088, compound

Product 1

HCID 12897090Methyl 5-chloro-1-methyl-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 5-chloropyrrole-3-carboxylate (800 mg., 5 mmoles) was dissolved in 75 ml. of ether. Sodium hydride (57% dispersion in oil, 430 mg., 10 mmoles) was added and the mixture stirred under nitrogen for 1 hour. Dimethyl sulfate (1 ml., 10.7 mmoles) was added and stirring continued for 2 hours. Excess sodium hydride was decomposed by cautious addition of 20 ml. of water. The ether phase was washed with 20 ml. of water and evaporated to yield methyl 1-methyl-5-chloropyrrole-3-carboxylate (oil); the entire batch being used directly in the next step.

Workup

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. washThe ether phase was washed with 20 ml
  4. customof water and evaporated

Sources & evidence

ORD record
ord-9efd94ac9d9b4841bafc0dfbb8881d09
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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