Reacción #1924610

Ecuación de reacción

Monochloroborane methyl sulfide

compound 10

6-(Dimethylsilanylmethyltrimethylsilanyl)hex-1-ene

THF

hydrogen peroxide

→

6-(Dimethyltrimethylsilanylmethylsilanyl)-hexan-1-ol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture stirred at 0° C. for 4 h
2. 2
   Lavadowashed with water
3. 3
   Extracciónthe organic layer extracted into hexane/ethyl acetate (3×30 ml, 1:1)
4. 4
   LavadoThe combined extracts were washed with brine
5. 5
   Secadodried (MgSO4)
6. 6
   Otrothe solvent removed in vacuo
7. 7
   Otroto yield colorless oil
8. 8
   OtroThe crude product was purified by column chromatography [silica gel eluted with hexane/ethyl acetate (4:1)]
9. 9
   Otroto yield a colorless oil

Procedimiento

Monochloroborane-methyl sulfide (2.03 ml, 2.15 g, 19.5 mmol) was added dropwise to a stirred, cooled (0° C.) solution of compound 10 (2.96 g, 13.0 mmol) in THF (20 ml). The reaction mixture was stirred at 0° C. for 24 h, and a solution of hydrogen peroxide (13 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 (MgSO4) 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.

Fuente