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

HRID 618313Notes

Reaction equation

HRID 618313 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-99771a53c7ad458abe01925b0d066d71
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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