Reacción #52061

Ecuación de reacción

(S)-3-(t-butyl dimethylsilyloxy)-5-(4-methoxy-benzyloxy)-1-phenyl pentane

DDQ

NaHCO3

→

(S)-3-(t-butyldimethylsilyloxy)-5-phenyl-pentan-1-ol

Rendimiento 99.4%

Disolventes

dichloromethane water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to the reaction solution
2. 2
   Otrothe reaction
3. 3
   OtroThe organic layer was separated
4. 4
   Extracciónthe aqueous layer was extracted with dichloromethane
5. 5
   Lavadowashed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
6. 6
   Secadodried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

Procedimiento

(S)-3-(t-butyl dimethylsilyloxy)-5-(4-methoxy-benzyloxy)-1-phenyl pentane (15 g, 36.2 mmol) was dissolved in a solvent mixture of dichloromethane-water (20:1) (252 ml). DDQ (8.2 g, 36.2 mmol) was added thereto and the mixture was stirred for 30 minutes at room temperature. After completion of the reaction, saturated aqueous NaHCO3 solution (100 ml) was added to the reaction solution to stop the reaction. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give (S)-3-(t-butyldimethylsilyloxy)-5-phenyl-pentan-1-ol (10.6 g, Yield 99%) of a yellow oil.

Fuente