Реакция #338902

Уравнение реакции

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

Выход 92.6%

Растворители

water

Условия реакции

Обработка

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
   ДругоеReaction solution
5. 5
   ДругоеAn aqueous layer was separated
6. 6
   Другоеremoved
7. 7
   Другоеsolvent was removed under reduced pressure
8. 8
   ДругоеSolid thus obtained
9. 9
   Другоеwas dried under reduced pressure

Методика

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%).

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