Réaction #654832

Équation de réaction

8-methyl-8-methoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene

hydrochloric acid

potassium hydroxide

lithium aluminum hydride

→

white solid

Rendement 82.4%

8-methyl-8-hydroxymethyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene

Rendement 82.4%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added from a dripping funnel over one hour
2. 2
   Autrefollowed by a reaction for 2.5 hours at 70° C
3. 3
   Températureto cool to room temperature
4. 4
   ExtractionThe reaction solution was then extracted with toluene
5. 5
   LavageThe salt-out product was washed several times with water
6. 6
   Séchagedried over anhydrous magnesium sulfate
7. 7
   AutreToluene was evaporated

Mode opératoire

37.6 g of lithium aluminum hydride and 800 ml of tetrahydrofuran were added to a flask and maintained at 0° C. in a nitrogen atmosphere. Then, 200 g of 8-methyl-8-methoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene dissolved in 200 ml of tetrahydrofuran was added from a dripping funnel over one hour, followed by a reaction for 2.5 hours at 70° C. The reaction solution was allowed to cool to room temperature and a 10% aqueous solution of potassium hydroxide was added gradually, followed by further addition of 10% aqueous solution of hydrochloric acid. The reaction solution was then extracted with toluene and the reaction product was salted out from saturated brine. The salt-out product was washed several times with water and dried over anhydrous magnesium sulfate. Toluene was evaporated to obtain 145 g of a white solid of 8-methyl-8-hydroxymethyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene shown by the following formula (19).

Source