반응 #50187

반응 방정식

3-bromofuran

tributyltin chloride

n-butyllithium

tetrahydrofuran

→

(3-furanyl)tributylstannane

용매

hexane

반응 조건

후처리

1. 1
   기타does not exceed -50° C.
2. 2
   workup.ADDITIONWhen the addition
3. 3
   기타to exceed -50° C.
4. 4
   workup.ADDITIONWhen the addition
5. 5
   기타to come to -10° C.
6. 6
   workup.STIRRINGis then stirred for one hour at that temperature
7. 7
   기타The solution is then carefully quenched with water
8. 8
   추출The aqueous phase is extracted with ethyl acetate
9. 9
   세척The organic phase is washed with saturated sodium chloride solution
10. 10
    건조dried over sodium sulphate
11. 11
    여과It is filtered off
12. 12
    기타the solvent is removed in vacuo
13. 13
    기타The crude product obtained
14. 14
    workup.DISTILLATIONis purified by distillation in a high vacuum

실험 절차

69.5 ml of a 1.6 molar solution of n-butyllithium in hexane are mixed with 60 ml of absolute tetrahydrofuran. The mixture is cooled to -60° C. and 10 ml of 3-bromofuran are added dropwise at such a rate that the internal temperature does not exceed -50° C.. When the addition is complete, the whole is stirred for 15 minutes at -60° C. and then 33.2 ml of tributyltin chloride are added dropwise, during the course of which the internal temperature is not allowed to exceed -50° C.. When the addition is complete, the reaction solution is allowed to come to -10° C. and is then stirred for one hour at that temperature. The solution is then carefully quenched with water. The aqueous phase is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried over sodium sulphate. It is filtered off and the solvent is removed in vacuo. The crude product obtained is purified by distillation in a high vacuum. 30.14 g of (3-furanyl)tributylstannane are obtained in the form of a light-yellow oil (boiling point=100°-104° C. at 0.09 torr).

출처