反应 #1857551

反应方程式

(S)-methyl 2-((S)-1-((4-methoxybenzyl)oxy)ethyl)-5-methylhexanoate

→

(S)-2-((S)-1-((4-methoxybenzyl)oxy)ethyl)-5-methylhexanal

溶剂

DCM

反应条件

后处理

1. 1
   其他at 0° C
2. 2
   其他The flask was removed from the cold bath
3. 3
   温度cooled
4. 4
   workup.ADDITIONmixture of diethyl ether (Et2O; 60 mL) and 2 Normal (N) HCl (20 mL) over 15 min
5. 5
   其他The mixture was removed from the cold bath
6. 6
   workup.STIRRINGstirred at room temperature for 30 min
7. 7
   其他The phases were separated
8. 8
   萃取the aq. phase was further extracted with Et2O (2×50 mL)
9. 9
   洗涤washed with sat. aq. sodium bicarbonate (NaHCO3; 25 mL) and brine (25 mL)
10. 10
    干燥dried over Na2SO4
11. 11
    过滤filtered
12. 12
    workup.ADDITIONthe filtrate treated with Celite® (5 scoopula tip-fulls)
13. 13
    其他The solvent was removed under reduced pressure
14. 14
    其他purified

实验过程

To a solution of (S)-methyl 2-((S)-1-((4-methoxybenzyl)oxy)ethyl)-5-methylhexanoate (6.00 g, 19.5 mmol) and chlorobis(cyclooctene)-iridium(I) dimer (0.349 g, 0.389 mmol) in dry DCM (19.5 mL) was slowly added Et2SiH (3.76 mL, 29.2 mmol) at 0° C. The flask was removed from the cold bath and the reaction was stirred at room temperature for 20 h under nitrogen (N2). The reaction mixture was transferred via cannula to an ice-cooled mixture of diethyl ether (Et2O; 60 mL) and 2 Normal (N) HCl (20 mL) over 15 min. The mixture was removed from the cold bath and stirred at room temperature for 30 min. The phases were separated and the aq. phase was further extracted with Et2O (2×50 mL). The organics were combined, washed with sat. aq. sodium bicarbonate (NaHCO3; 25 mL) and brine (25 mL), dried over Na2SO4, filtered, and the filtrate treated with Celite® (5 scoopula tip-fulls). The solvent was removed under reduced pressure and the resulting adsorbed material was directly loaded onto a column and purified using flash column chromatography (120 g SiO2, 0→75% EtOAc/hexanes) to afford the intermediate aldehyde, (S)-2-((S)-1-((4-methoxybenzyl)oxy)ethyl)-5-methylhexanal.

来源