Reaktion #501079

Reaktionsgleichung

tosic acid

N,N-Dimethyl-1,3-phenylenediamine dihydrochloride

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

triethylamine

→

product

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

Lösungsmittel

methylene chloride

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux
3. 3
   Waschenwashed with water, 5% sodium bicarbonate, and brine
4. 4
   TrocknenThe organic layer was dried over NaSO4
5. 5
   Sonstigethe solids were separated
6. 6
   Sonstigethe solvents removed under vacuum
7. 7
   SonstigeThe crude material was purified over silica gel

Vorschrift

N,N-Dimethyl-1,3-phenylenediamine dihydrochloride (5 mmol, 1.0 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5 mmol, 1.2 g), triethylamine (10 mmol, 1.0 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in methylene chloride, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO4, then the solids were separated and the solvents removed under vacuum. The crude material was purified over silica gel and yielded the named product (m.p. 111.7° C.-114° C.).

Quelle