反应 #1924609

反应方程式

Monochloroborane methyl sulfide

compound 9

8-(Dimethylsilanylmethyltrimethylsilanyl)oct-1-ene

hydrogen peroxide

→

8-(Dimethylsilanylmethyltrimethylsilanyl)octan-1-ol

溶剂

THF

反应条件

后处理

1. 1
   workup.STIRRINGthe reaction mixture stirred at 0° C. for 4 h
2. 2
   洗涤washed with water
3. 3
   萃取the organic layer extracted into hexane/ethyl acetate (3×30 ml, 1:1)
4. 4
   洗涤The combined extracts were washed with brine
5. 5
   其他dried (MgS04)
6. 6
   其他the solvent removed in vacuo
7. 7
   其他to yield colorless oil
8. 8
   其他The crude product was purified by column chromatography [silica gel eluted with hexane/ethyl acetate (4:1)]
9. 9
   其他to yield a colorless oil

实验过程

Monochloroborane-methyl sulfide (1.10 ml, 1.16 g, 10.5 mmol) was added dropwise to a stirred, cooled (0° C.) solution of compound 9 (2.56 g, 10.0 mmol) in THF (30 ml). The reaction mixture was stirred at 0° C. for 24 h, and a solution of hydrogen peroxide (10 ml, 30% in water) added dropwise and the reaction mixture stirred at 0° C. for 4 h, washed with water and the organic layer extracted into hexane/ethyl acetate (3×30 ml, 1:1). The combined extracts were washed with brine, dried (MgS04) and the solvent removed in vacuo to yield colorless oil. The crude product was purified by column chromatography [silica gel eluted with hexane/ethyl acetate (4:1)] to yield a colorless oil.

来源