Sodium Hydroxide → HCID 19371039, compound

HRID 129330Notes

Reaction equation

HRID 129330 reaction equation
[OH-].[Na+].[CH2:3]([C:17]1[NH:21][CH:20]=[C:19]([C:22]([O:24]CC)=[O:23])[CH:18]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C(O)C>[CH2:3]([C:17]1[NH:21][CH:20]=[C:19]([C:22]([OH:24])=[O:23])[CH:18]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19371040HCID 19371040, compound

Product 1

HCID 19371039HCID 19371039, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of 1N sodium hydroxide (25 ml) was added to an ethanol solution (120 ml) of 3.53 g (11 mmol) of ethyl 5-tetradecylpyrrole-3-carboxylate, and the whole was heated under reflux for 16 hours. After removal of the ethanol, the residue was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The extract was then washed with water and dried over anhydrous magnesium sulfate. The residue was purified by subjecting it to silica gel column chromatography (eluent: ethyl acetate/hexane=1/4) to obtain 2.19 g (68% yield) of 5-tetradecylpyrrole-3-carboxylic acid, m.p. 83°-85° C.

Workup

  1. temperaturethe whole was heated
  2. temperatureunder reflux for 16 hours
  3. customAfter removal of the ethanol
  4. extractionextracted with ethyl acetate
  5. washThe extract was then washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe residue was purified

Sources & evidence

ORD record
ord-d42cbc80be894a339141367e27596432
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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