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

HRID 1770369노트

반응식

HRID 1770369 반응식
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C@H:9]([C@H:11]([CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:12](OC)=[O:13])[CH3:10])=[CH:5][CH:4]=1>C(Cl)Cl.C1CCCC=CCC1.C1CCCC=CCC1.C1CCCC=CCC1.C1CCCC=CCC1.[Cl-].[Cl-].[Ir].[Ir]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C@H:9]([C@H:11]([CH2:16][CH2:17][CH:18]([CH3:19])[CH3:20])[CH:12]=[O:13])[CH3:10])=[CH:21][CH:22]=1

참가 물질

4

반응물 1

HCID 118194659(S)-methyl 2-((S)-1-((4-methoxybenzyl)oxy)ethyl)-5-methylhexanoate

생성물 1

HCID 118194695(S)-2-((S)-1-((4-methoxybenzyl)oxy)ethyl)-5-methylhexanal

시약·촉매·용매 2

HCID 91972094Chlorobis(cyclooctene)iridium(I) dimer촉매HCID 6344Dichloromethane용매

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.

후처리

  1. customat 0° C
  2. customThe flask was removed from the cold bath
  3. temperaturecooled
  4. additionmixture of diethyl ether (Et2O; 60 mL) and 2 Normal (N) HCl (20 mL) over 15 min
  5. customThe mixture was removed from the cold bath
  6. stirringstirred at room temperature for 30 min
  7. customThe phases were separated
  8. extractionthe aq. phase was further extracted with Et2O (2×50 mL)
  9. washwashed with sat. aq. sodium bicarbonate (NaHCO3; 25 mL) and brine (25 mL)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. additionthe filtrate treated with Celite® (5 scoopula tip-fulls)
  13. customThe solvent was removed under reduced pressure
  14. custompurified

출처 및 근거

ORD 기록
ord-0f38169136074e08a236cff97b848483
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09247741B2

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