Reaktion #426903

Reaktionsgleichung

Ethyl 1,2-dimethyl-5-phenyl-1H-pyrrole-3-carboxylic acid

NaOH

→

title compound

Ausbeute 95.0%

1,2-Dimethyl-5-phenyl-1H-pyrrole-3-carboxylic acid

Ausbeute 95.0%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 1 day with LC-MS monitoring
2. 2
   SonstigeAfter reaction complete
3. 3
   SonstigeEtOH was evaporated under reduced pressure
4. 4
   workup.ADDITIONWater (50 ml) was added
5. 5
   Waschenwashed aqueous layer with diethyl ether twice
6. 6
   workup.ADDITION1N HCl solution was added to aqueous layer until pH<3
7. 7
   ExtraktionAnd extraction
8. 8
   TrocknenOrganic layer was dried with MgSO4
9. 9
   Sonstigeevaporated in vacuo

Vorschrift

To the solution of Ethyl 1,2-dimethyl-5-phenyl-1H-pyrrole-3-carboxylic acid (3 g, 13 mmol) in EtOH (50 ml) was added NaOH (1.6 g, 39 mmol) at room temperature. The reaction mixture was refluxed for 1 day with LC-MS monitoring. After reaction complete, EtOH was evaporated under reduced pressure. Water (50 ml) was added and washed aqueous layer with diethyl ether twice. 1N HCl solution was added to aqueous layer until pH<3. And extraction was accomplished with EtOAc. Organic layer was dried with MgSO4 and evaporated in vacuo to provide title compound (2.6 g, 95%) as yellow soild. Without further purification, acid was used for the reaction of amide coupling.

Quelle