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

HRID 842181

Reaction equation

HRID 842181 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]([CH2:19][C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16](=O)[CH3:17])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:19]=[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[O:10])[CH3:9])[CH:3]=2)[C:16]=1[CH3:17])=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74173'-AminoacetophenoneHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 102913571-(3-Acetylphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3′-Aminoacetophenone (5 mmol, 0.7 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (5 mmol, 1.2 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was purified over silica and yielded the named product as a solid (m.p. 102° C.-104° C.).

Workup

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

Sources & evidence

ORD record
ord-21d844b6be9d4ead8f7b8716ebc6bcb6
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Linked notes

Loading…