反応 #50187

反応方程式

3-bromofuran

tributyltin chloride

n-butyllithium

tetrahydrofuran

→

(3-furanyl)tributylstannane

溶媒

hexane

反応条件

後処理

1. 1
   その他does not exceed -50° C.
2. 2
   workup.ADDITIONWhen the addition
3. 3
   その他to exceed -50° C.
4. 4
   workup.ADDITIONWhen the addition
5. 5
   その他to come to -10° C.
6. 6
   workup.STIRRINGis then stirred for one hour at that temperature
7. 7
   その他The solution is then carefully quenched with water
8. 8
   抽出The aqueous phase is extracted with ethyl acetate
9. 9
   洗浄The organic phase is washed with saturated sodium chloride solution
10. 10
    乾燥dried over sodium sulphate
11. 11
    ろ過It is filtered off
12. 12
    その他the solvent is removed in vacuo
13. 13
    その他The crude product obtained
14. 14
    workup.DISTILLATIONis purified by distillation in a high vacuum

実験手順

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).

出典