反应 #213919

反应方程式

magnesium

propargyl bromide

1,1-dimethoxy-2-hexanone

imidazole

trimethylchlorosilane

1,2-dibromoethane

ammonium chloride

magnesium sulfate

→

title compound

4-Dimethoxymethyl-4-trimethylsiloxy-1-octyne

溶剂

ether

tetrahydrofuran

water

ether

ether

反应条件

后处理

1. 1
   workup.ADDITIONTo a suspension of 5.31 g
2. 2
   workup.ADDITIONfollowed by the dropwise addition of a solution of 25 g
3. 3
   workup.ADDITIONMidway through the addition 15 ml
4. 4
   workup.ADDITIONAfter complete addition of the solution
5. 5
   温度the mixture is refluxed for 40 minutes
6. 6
   过滤The mixture is filtered through Celite
7. 7
   其他the solvent is removed
8. 8
   workup.DISSOLUTIONThe residue is dissolved in 53 ml
9. 9
   workup.ADDITIONof dimethylformamide and at 0° C. is added 24.4 g
10. 10
    萃取extracted with hexanes
11. 11
    干燥The organic layer is dried over magnesium sulfate
12. 12
    其他the solvent is removed
13. 13
    workup.DISTILLATIONDistillation (75°-95° C., 0.3 mm.)
14. 14
    其他gives 17.4 g

实验过程

To a suspension of 5.31 g. (0.22 moles) of magnesium in 15 ml. of ether is added 100 mg. of mercuric chloride and 1.5 ml. of 1,2-dibromoethane. After the reaction begins, another 45 ml. of ether is added followed by the dropwise addition of a solution of 25 g. (0.16 moles) of 1,1-dimethoxy-2-hexanone and 27.3 g. (0.2 moles) of 85% propargyl bromide in 45 ml. of ether at a rate which maintains reflux. Midway through the addition 15 ml. of tetrahydrofuran is added. After complete addition of the solution, the mixture is refluxed for 40 minutes. The mixture is cooled to 0° C. and saturated ammonium chloride solution is added followed by magnesium sulfate. The mixture is filtered through Celite and the solvent is removed. The residue is dissolved in 53 ml. of dimethylformamide and at 0° C. is added 24.4 g. (0.36 moles) of imidazole and 21.19 g. (0.20 moles) of trimethylchlorosilane. After stirring at 25° C. for 70 minutes, the solution is poured into water and extracted with hexanes. The organic layer is dried over magnesium sulfate and the solvent is removed. Distillation (75°-95° C., 0.3 mm.) gives 17.4 g. of the title compound.

来源