반응 #819503

반응 방정식

hydrochloric acid

potassium t-butoxide

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

ethyl isocyanoacetate

→

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

수율 80.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the system
2. 2
   기타over 2 hours
3. 3
   세척The reaction mixture was then washed in turn with saturated aqueous sodium bicarbonate solution
4. 4
   workup.DISTILLATIONdistilled water and saturated saline
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The resulting product was purified

실험 절차

The reaction system of a mixture liquid 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 nitrogen, and 2.425 ml (22 mmol) of ethyl isocyanoacetate was added to the system then cooled to 0° C. After dropping potassium t-butoxide (50 ml/1 M THF solution) over 2 hours, the solution was stirred for 3 hours. After the reaction was finished, dilute hydrochloric acid was added. The reaction mixture was then washed in turn with saturated aqueous sodium bicarbonate solution, 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, 1.6 mmol, yield 80%).

출처