Hydrochloric Acid → Ethyl 5-tridecanoylpyrrole-3-carboxylate

HRID 1090732Notes

Reaction equation

HRID 1090732 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:2]1.[C:11](Cl)(=[O:24])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(O)(=O)CCCCCCCCCCCC.Cl>C1C=CC=CC=1>[C:11]([C:5]1[NH:1][CH:2]=[C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=1)(=[O:24])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12530Tridecanoic acidHCID 87288Tridecanoyl chlorideHCID 13070719Ethyl 1H-pyrrole-3-carboxylate

Product 1

HCID 15023254Ethyl 5-tridecanoylpyrrole-3-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution (20 ml) of 2.78 g (20 mmol) of ethyl pyrrole-3-carboxylate in benzene was added tridecanoyl chloride prepared from 4.28 g (20 mml) of tridecanoic acid in a conventional manner, followed by further dropwise addition of 3.5 ml (30 mmol) of stannic chloride. After the addition, the mixture was stirred for 15 hours at room temperature, treated with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by subjecting it to silica gel column chromatography (eluent: ethyl acetate/hexane=1/7) to obtain 4.85 g (72% yield) of ethyl 5-tridecanoylpyrrole-3-carboxylate.

Workup

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the solvent under reduced pressure
  6. customthe residue was purified

Sources & evidence

ORD record
ord-a4994531f3364fad986a0d346595f583
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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