Sodium Hydroxide → HCID 15023299, compound

HRID 1090727Notes

Reaction equation

HRID 1090727 reaction equation
[CH2:1]([C:15]1[NH:19][C:18]([C:20]([O:22]CC)=[O:21])=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[OH-].[Na+]>C(O)C>[CH2:1]([C:15]1[NH:19][C:18]([C:20]([OH:22])=[O:21])=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15023300HCID 15023300, compound

Product 1

HCID 15023299HCID 15023299, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-tetradecylpyrrole-2-carboxylate obtained in Example 1 (0.50 g, 1.5 mmol) was dissolved in 20 ml of ethanol followed by adding 3 ml (3 mmol) of aqueous 1N sodium hydroxide solution thereto. The resulting mixture was heated under reflux for 6 hours. After cooling the mixture, precipitates were filtered, washed well with ether, suspended in diluted hydrochloric acid, and extracted with ether. The extract was further washed with an aqueous saturated solution of sodium chloride and dried over anhydrous megnesium sulfate. A removal of the solvent under reduced pressure afforded 0.34 g (74% yield) of 5-tetradecylpyrrole-2-carboxylic acid, m.p. 68°-69° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling the mixture
  4. customprecipitates
  5. filtrationwere filtered
  6. washwashed well with ether
  7. extractionextracted with ether
  8. washThe extract was further washed with an aqueous saturated solution of sodium chloride
  9. dry with materialdried over anhydrous megnesium sulfate
  10. customA removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ca1b2166cfd74454b26f0a6a79794e6c
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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