Potassium Hydroxide → HCID 66915113, compound

HRID 880436Notes

Reaction equation

HRID 880436 reaction equation
[OH-].[K+].[Br:3][C:4]1[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([C:11]([O:13]CC)=[O:12])[N:7]([CH3:10])[C:8]=1[CH3:9]>O.C(O)C>[Br:3][C:4]1[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([C:11]([OH:13])=[O:12])[N:7]([CH3:10])[C:8]=1[CH3:9]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 66914796HCID 66914796, compound

Product 1

HCID 66915113HCID 66915113, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (1.40 g, 25.0 mmol) in water (3 mL) was added to a solution of ethyl 4-bromo-1,5-dimethyl-3-phenyl-pyrrole-2-carboxylate (1.60 g, 4.97 mmol) in ethanol (5 mL) and the reaction mixture was refluxed overnight. The solvent was evaporated and the residue was washed with diethyl ether. The resultant filter cake was acidified with diluted HCl and extracted with ether. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4-bromo-1,5-dimethyl-3-phenyl-pyrrole-2-carboxylic acid (1.0 g, 69%) as a solid.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe solvent was evaporated
  3. washthe residue was washed with diethyl ether
  4. filtrationThe resultant filter cake
  5. extractionextracted with ether
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0881e58ac8ee473089ee1867f899d600
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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