Reaktion #501070

ord-210abc33d9694858aad349bfe1d0f800

Reaktionsgleichung

Cc1cccc(N)c1
m-Toluidine
CCOC(=O)C(CC(C)=O)C(=O)c1ccccc1
2-benzoyl-4-oxo-pentanoic acid ethyl ester
Cc1ccc(S(=O)(=O)O)cc1
tosic acid
→
CCOC(=O)c1cc(C)n(-c2cccc(C)c2)c1-c1ccccc1
product
CCOC(=O)c1cc(C)n(-c2cccc(C)c2)c1-c1ccccc1
5-Methyl-2-phenyl-1-m-tolyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester

Edukte

Cc1cccc(N)c1
m-Toluidine
CCOC(=O)C(CC(C)=O)C(=O)c1ccccc1
2-benzoyl-4-oxo-pentanoic acid ethyl ester
Cc1ccc(S(=O)(=O)O)cc1
tosic acid

Reagenzien

Keine

Lösungsmittel

CCO
ethanol
ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

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 (sodium sulfate)
  5. 5
    Sonstigethe solids were separated
  6. 6
    Sonstigethe solvents evaporated under vacuum
  7. 7
    SonstigeThe crude product was recrystallized from ethanol

Vorschrift

m-Toluidine (5 mmol, 0.5 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 resulting oil was resuspended in methylene chloride, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO4 (sodium sulfate), the solids were separated, and the solvents evaporated under vacuum. The crude product was recrystallized from ethanol to yield the named product (m.p. 92.5° C.-94.0° C.).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06569890B2uspto-grants-2003_05