1-Bromopropane → Methyl 1-propylpyrrole-2-carboxylate

HRID 1701521Notes

Reaction equation

HRID 1701521 reaction equation
[OH-].[K+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([O:10][CH3:11])=[O:9].Br[CH2:13][CH2:14][CH3:15]>CS(C)=O>[CH2:13]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([O:10][CH3:11])=[O:9])[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 14797Potassium HydroxideHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 20346897Methyl 1-propylpyrrole-2-carboxylateYield 74.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 9 g potassium hydroxide in 25 ml dimethylsulfoxide are added 5 g methyl pyrrole-2 carboxylate and 10 g 1-bromo-propane. After stirring for one hour, the reaction mixture is poured over 100 g crushed ice, after which the solution is extracted with ethyl ether. After drying, the solvent is evaporated under reduced pressure, to give 5 g crude methyl 1-propyl-pyrrole-2-carboxylate.

Workup

  1. additionthe reaction mixture is poured over 100 g
  2. customcrushed ice
  3. extractionafter which the solution is extracted with ethyl ether
  4. customAfter drying
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-fcfde33076b84b9eac1174408fcf1f41
Source dataset
uspto-grants-1980_03
Patent number
US04194003

Reaction notes

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