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

HRID 602721Notes

Reaction equation

HRID 602721 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) δ 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-2274a5ab22434a2da0e693ffa79854ab
Source dataset
uspto-grants-2011_03
Patent number
US07906550B2

Reaction notes

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