Reacción #90285

Ecuación de reacción

ethyl 5-(3,4-bis(benzyloxy)-5-nitrophenyl)-1-methyl-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-pyrrole-3-carboxylate

boron tribromide

→

ethyl 5-(3,4-dihydroxy-5-nitrophenyl)-1-methyl-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-pyrrole-3-carboxylate

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGto stir at room temperature for one hour
2. 2
   OtroThe mixture was quenched by the careful addition of methanol
3. 3
   workup.STIRRINGAfter stirring at room temperature for thirty minutes
4. 4
   Otrothe volatiles were evaporated
5. 5
   workup.STIRRINGthe residue stirred with 2 N hydrochloric acid (5 mL) for thirty minutes
6. 6
   FiltraciónThe resulting solid was filtered off
7. 7
   Lavadowashed with water (25 mL)

Procedimiento

A solution of ethyl 5-(3,4-bis(benzyloxy)-5-nitrophenyl)-1-methyl-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-pyrrole-3-carboxylate (0.189 g, 0.30 mmol) in dichloromethane (10 mL) was cooled to −78° C. with stirring and treated under argon with boron tribromide (0.30 g, 1.21 mmol). The resulting deep purple suspension was then allowed to stir at room temperature for one hour before cooling again to −78° C. The mixture was quenched by the careful addition of methanol. After stirring at room temperature for thirty minutes, the volatiles were evaporated and the residue stirred with 2 N hydrochloric acid (5 mL) for thirty minutes. The resulting solid was filtered off, washed with water (25 mL) and then cold isopropanol (5 mL) to give ethyl 5-(3,4-dihydroxy-5-nitrophenyl)-1-methyl-2-(2-(trifluoromethyl)pyridin-3-yl)-1H-pyrrole-3-carboxylate as a yellow solid, 0.126 g (93%).

Fuente