反応 #52061

反応方程式

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

DDQ

NaHCO3

→

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

収率 99.4%

溶媒

dichloromethane water

反応条件

後処理

1. 1
   workup.ADDITIONwas added to the reaction solution
2. 2
   その他the reaction
3. 3
   その他The organic layer was separated
4. 4
   抽出the aqueous layer was extracted with dichloromethane
5. 5
   洗浄washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
6. 6
   乾燥dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

実験手順

(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.

出典