Hydrochloric Acid → Ethyl 4-tridecylpyrrole-2-carboxylate

HRID 129347Notes

Reaction equation

HRID 129347 reaction equation
[H-].[Na+].[CH2:3]([C:16]1[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[NH:19][CH:20]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].Cl.[CH3:25][CH2:26]CCCC>CN(C)C=O>[CH2:3]([C:16]1[CH:17]=[C:18]([C:21]([O:23][CH2:25][CH3:26])=[O:22])[NH:19][CH:20]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 24758Sodium hydrideHCID 99480484-Tridecylpyrrole-2-carboxylic acid

Product 1

HCID 15023275Ethyl 4-tridecylpyrrole-2-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After washing 140 mg (3.50 mmol) of 60% sodium hydride with hexane, 20 ml of dimethylformamide was added thereto, and then 90 mg (3.38 mmol) of 4-tridecylpyrrole-2-carboxylic acid prepared in Example 2 was further added portionwise under stirring at room temperature. After stirring for 10 minutes, 5.0 g (31.8 mmol) of ethyl idodide was added to the reaction solution followed by heating it at 55° C. for 22 hours. After cooling, an aqueous solution of hydrochloric acid was added to acidify the mixture, and the resulting mixture was then extracted with ethyl acetate, washed with an aquous saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/10) to obtain 600 mg (55% yield) of ethyl 4-tridecylpyrrole-2-carboxylate as white crystals, m.p. 59°-60° C.

Workup

  1. additionwas added
  2. stirringAfter stirring for 10 minutes
  3. addition5.0 g (31.8 mmol) of ethyl idodide was added to the reaction solution
  4. temperatureby heating it at 55° C. for 22 hours
  5. temperatureAfter cooling
  6. extractionthe resulting mixture was then extracted with ethyl acetate
  7. washwashed with an aquous saturated solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter removing the solvent under reduced pressure
  10. customthe residue was purified

Sources & evidence

ORD record
ord-8f6f939e253643a7bbc7bb74147bd243
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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