Potassium Hydroxide → 3-Acetyl-4,5-dimethyl-1H-pyrrole-2-carboxylic acid

HRID 902196Notes

Reaction equation

HRID 902196 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:15])=[C:9]([CH3:14])[C:10]=1[C:11](=[O:13])[CH3:12])=[O:5])C.[OH-].[K+]>C(O)C>[C:11]([C:10]1[C:9]([CH3:14])=[C:8]([CH3:15])[NH:7][C:6]=1[C:4]([OH:5])=[O:3])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12288399Ethyl 3-acetyl-4,5-dimethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 5906793-Acetyl-4,5-dimethyl-1H-pyrrole-2-carboxylic acidYield 81.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of pyrrole ester 34 (8.2 g, 0.0392 mol), in ethanol and 100 mL of 10% potassium hydroxide were refluxed for 1 h. The mixture was cooled and concentrated in vacuo to an oil. Water was added to the oil, the mixture acidified with dilute HCl and extracted with ether. The organic phase was dried with anhy. sodium sulfate and concentrated in vacuo to a solid residue. The compound was recrystallized in 80 mL of ethanol to give 5.8 g of pure 3-acetyl-4,5-dimethyl-2-pyrrole carboxylic acid 35 as a solid. 1H NMR (DMSO-d6) d 2.5 (s,3H), 2.2 (s,3H), 2.0 (s,3H) ppm.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo to an oil
  3. additionWater was added to the oil
  4. extractionextracted with ether
  5. customThe organic phase was dried with anhy
  6. concentrationsodium sulfate and concentrated in vacuo to a solid residue
  7. customThe compound was recrystallized in 80 mL of ethanol

Sources & evidence

ORD record
ord-fb94e4ba5f154b89b3fedfe73a2f6b6b
Source dataset
uspto-grants-2008_04
Patent number
US07365092B2

Reaction notes

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