Sodium Hydroxide → 4-phenyl-1H-pyrrole-2-carboxylic acid

HRID 880432Notes

Reaction equation

HRID 880432 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:12]([O:14]CC)=[O:13])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([C:7]2[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[NH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14643813Ethyl 4-phenyl-1H-pyrrole-2-carboxylate

Product 1

HCID 128971004-phenyl-1H-pyrrole-2-carboxylic acidYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-phenyl-1H-pyrrole-2-carboxylate (700 mg, 3.25 mmol), aqueous sodium hydroxide (10% w/v, 10 mL) and ethanol (10 mL) were stirred at room temperature over night. The ethanol was evaporated in vacuo, then water (20 mL) was added and the organics were extracted with ethyl acetate (3×20 mL). The aqueous layer was acidified with 2N HCl (to pH 3) and extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with water, brine (20 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 4-phenyl-1H-pyrrole-2-carboxylic acid (400 mg, 66%) as a solid.

Workup

  1. customThe ethanol was evaporated in vacuo
  2. additionwater (20 mL) was added
  3. extractionthe organics were extracted with ethyl acetate (3×20 mL)
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. washThe combined organic layer was washed with water, brine (20 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d3e196acd714c4690d354282c61aa0e
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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