반응 #52061

반응 방정식

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

DDQ

NaHCO3

→

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

수율 99.4%

용매

dichloromethane water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the reaction solution
2. 2
   기타the reaction
3. 3
   기타The organic layer was separated
4. 4
   추출the aqueous layer was extracted with dichloromethane
5. 5
   세척washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

실험 절차

(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.

출처