p-Toluenesulfonic acid → 1-(3-Acetylphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 842180Notes

Reaction equation

HRID 842180 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11]([O:13][C:14](=[O:28])[CH:15]([C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][C:17](=O)[CH3:18])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:16]=[C:17]([CH3:18])[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[O:10])[CH3:9])[CH:3]=2)[C:20]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74173'-AminoacetophenoneHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 102913581-(3-Acetylphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3′-Amino-acetophenone (5 mmol, 0.7 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5 mmol, 1.2 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The residual oil was purified over silica and yielded the named product (m.p. 100° C.-102° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe residual oil was purified over silica

Sources & evidence

ORD record
ord-872fa4e819a249b38b0fdd127ee84d60
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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