반응 #1857551

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

→

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

용매

DCM

반응 조건

후처리

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

실험 절차

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.

출처