Hydrochloric Acid → Ethyl 5-tridecanoylpyrrole-3-carboxylate

HRID 129331

Reaction equation

HRID 129331 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-6c3d7b82a9c6450b918fe490c99f6adc
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Linked notes

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