Reaktion #501080

Reaktionsgleichung

m-Iodoaniline

2-benzoyl-4-oxo-pentanoic acid ethyl ester

tosic acid

→

product

1-(3-Iodophenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester

Lösungsmittel

ethanol

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux
3. 3
   Waschenwashed with water, 5% sodium bicarbonate, and brine
4. 4
   SonstigeThe solids were separated
5. 5
   Sonstigethe solvents removed under vacuum
6. 6
   SonstigeThe resulting solid was recrystallized in ethanol
7. 7
   workup.DISSOLUTIONA portion of the material did not dissolve
8. 8
   Sonstigewas separated by filtration
9. 9
   SonstigeBoth the recrystallized
10. 10
    Filtrationfiltered material

Vorschrift

m-Iodoaniline (5 mmol, 1.1 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 resuspended in methylene chloride, then washed with water, 5% sodium bicarbonate, and brine. The solids were separated, and the solvents removed under vacuum. The resulting solid was recrystallized in ethanol. A portion of the material did not dissolve, and was separated by filtration. Both the recrystallized and filtered material yielded the named product (m.p. 142.6° C.-144° C.).

Quelle