Sodium Hydroxide → HCID 15023289, compound

HRID 129333Notes

Reaction equation

HRID 129333 reaction equation
[CH2:1]([C:14]1[NH:18][CH:17]=[C:16]([C:19]([O:21]CC)=[O:20])[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH-].[Na+]>C(O)C>[CH2:1]([C:14]1[NH:18][CH:17]=[C:16]([C:19]([OH:21])=[O:20])[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15023291HCID 15023291, compound

Product 1

HCID 15023289HCID 15023289, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (40 ml) of 2.60 g (8.1 mmol) of ethyl 5-tridecylpyrrole-3-carboxylate prepared in Example 5 was added 10 ml of an aqueous solution containing 1.40 g (33 mmol) of sodium hydroxide. The mixture was heated under reflux for 36 hours. After removing the ethanol, the mixture was acidified with hydrochloric acid, extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give crystals, which were purified by subjecting them to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/2) to obtain 2.04 g (86% yield) of pure 5-tridecylpyrrole-3-carboxylic acid, m.p. 82°-84° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 36 hours
  3. customAfter removing the ethanol
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give crystals, which
  8. customwere purified

Sources & evidence

ORD record
ord-6bfa09ae24064e35986fe8de6a0358ac
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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