Benzoyl chloride → Ethyl (5-benzoyl-1,4-dimethyl-1H-pyrrol-2-yl)acetate

HRID 369378Notes

Reaction equation

HRID 369378 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>>[C:14]([C:6]1[N:2]([CH3:1])[C:3]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:5]=1[CH3:7])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 15870188Ethyl (5-benzoyl-1,4-dimethyl-1H-pyrrol-2-yl)acetateYield 57%

Procedure

Ethyl 1,4-dimethylpyrrole-2-acetate (37.0 g, 0.19 mol), benzoyl chloride (54.3 g, 0.38 mol), and triethylamine (52.9 ml, 0.38 mol) were dissolved in xylenes (750 ml), and the reaction mixture was refluxed for 18 h under argon. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. Purification on a Florisil® column (hexane followed by hexane-ethyl acetate, 4:1) gave ethyl 5-benzoyl-1,4-dimethylpyrrole-2-acetate (30.45 g, 57%) as a solid. ##STR19##

Workup

  1. temperaturethe reaction mixture was refluxed for 18 h under argon
  2. customthe solvent was removed in vacuo
  3. customPurification on a Florisil® column (hexane followed by hexane-ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-4c98e30111764e689b4d019bebc4a9f0
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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