Sodium Hydroxide → 1-(2-Carboxyethyl)-4-phenylpyrrole-2-carboxylic acid

HRID 880442Notes

Reaction equation

HRID 880442 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:25])[CH2:7][CH2:8][N:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[C:10]1[C:20]([O:22]CC)=[O:21])C>C(O)C>[C:6]([CH2:7][CH2:8][N:9]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:11]=[C:10]1[C:20]([OH:22])=[O:21])([OH:25])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66914703Ethyl 1-(3-ethoxy-3-oxopropyl)-4-phenylpyrrole-2-carboxylate

Product 1

HCID 669149081-(2-Carboxyethyl)-4-phenylpyrrole-2-carboxylic acidYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

10% Aqueous sodium hydroxide solution (20 mL) was added to a stirred solution of ethyl 1-(3-ethoxy-3-oxo-propyl)-4-phenyl-pyrrole-2-carboxylate (2.0 g, 6.35 mmol) in ethanol (20 mL). The reaction mixture was stirred for 2 h at 50-60° C. The ethanol was evaporated in vacuo and then water added to the residue and acidified with 5N HCl to pH 4-5. The precipitated solid was filtered, washed with water and dried in vacuo to afford 1-(2-carboxyethyl)-4-phenyl-pyrrole-2-carboxylic acid (900 mg, 56%) as a solid.

Workup

  1. customThe ethanol was evaporated in vacuo
  2. additionwater added to the residue
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-993b7679597248fa988734d46ebdacbd
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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