반응 #1924609

반응 방정식

Monochloroborane methyl sulfide

compound 9

8-(Dimethylsilanylmethyltrimethylsilanyl)oct-1-ene

hydrogen peroxide

→

8-(Dimethylsilanylmethyltrimethylsilanyl)octan-1-ol

용매

THF

반응 조건

후처리

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

실험 절차

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.

출처