Réaction #338902

Équation de réaction

3,3′-bis(2,2′-dibromoethyl)-5,5′,7,7′-tetramethyl-1,1′-biadamantane

potassium tert-butoxide

→

3,3′-diethynyl-5,5′,7,7′-tetramethyl-1,1′-biadamantane

Rendement 92.6%

Solvants

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere charged in a 500 mL recovery flask
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.STIRRINGthe mixture was agitated at room temperature for 48 hours
4. 4
   AutreReaction solution
5. 5
   AutreAn aqueous layer was separated
6. 6
   Autreremoved
7. 7
   Autresolvent was removed under reduced pressure
8. 8
   AutreSolid thus obtained
9. 9
   Autrewas dried under reduced pressure

Mode opératoire

Next, 63.4 g of the 3,3′-bis(2,2′-dibromoethyl)-5,5′,7,7′-tetramethyl-1,1′-biadamantane obtained above (90.9 mmol), 200 ml of N,N-dimethylsulfoxide and a stirrer were charged in a 500 mL recovery flask. Under nitrogen flow, 28 g of potassium tert-butoxide (250 mmol) was added with agitating at room temperature. After the addition, the mixture was agitated at room temperature for 48 hours. Reaction solution was added to 400 mL of ion-exchange water. An aqueous layer was separated and removed therefrom, and solvent was removed under reduced pressure. Solid thus obtained was dried under reduced pressure, thus obtaining 31.5 g of 3,3′-diethynyl-5,5′,7,7′-tetramethyl-1,1′-biadamantane (84.1 mmol; yield: 92.5%).

Source