反応 #1857551

反応方程式

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

→

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

溶媒

DCM

反応条件

後処理

1. 1
   その他at 0° C
2. 2
   その他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
   その他The mixture was removed from the cold bath
6. 6
   workup.STIRRINGstirred at room temperature for 30 min
7. 7
   その他The phases were separated
8. 8
   抽出the aq. phase was further extracted with Et2O (2×50 mL)
9. 9
   洗浄washed with sat. aq. sodium bicarbonate (NaHCO3; 25 mL) and brine (25 mL)
10. 10
    乾燥dried over Na2SO4
11. 11
    ろ過filtered
12. 12
    workup.ADDITIONthe filtrate treated with Celite® (5 scoopula tip-fulls)
13. 13
    その他The solvent was removed under reduced pressure
14. 14
    その他purified

実験手順

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.

出典