Reacción #2510566

Ecuación de reacción

potassium t-butoxide

5,6-bis(phenylsulfonyl)-bicyclo[2.2.2]octa-2-ene

ethyl isocyanoacetate

hydrochloric acid

→

ethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate

Rendimiento 80.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to the system, which
2. 2
   Otroover 2 hours
3. 3
   LavadoThe reaction mixture was then washed in turn with saturated aqueous sodium bicarbonate
4. 4
   workup.DISTILLATIONdistilled water and saturated saline
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   OtroThe resulting product was purified

Procedimiento

The reaction system of a mixed solution of 7.76 g (20 mmol) of the obtained 5,6-bis(phenylsulfonyl)-bicyclo[2.2.2]octa-2-ene and 50 ml of anhydrous tetrahydrofuran was purged with a nitrogen gas, and 2.425 (22 mmol) of ethyl isocyanoacetate was added to the system, which was then cooled to 0° C. After dropping potassium t-butoxide (50 ml/1M THF solution) over 2 hours, the solution was stirred for 3 hours. After the reaction was finished, dilute hydrochloric acid was added to the solution. The reaction mixture was then washed in turn with saturated aqueous sodium bicarbonate, distilled water and saturated saline, and dried over anhydrous sodium sulfate. The resulting product was purified using silica gel column chromatography (chloroform) to give ethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate (3.5 g, 16 mmol, yield 80%).

Fuente