Water → (S)-3-(t-butyldiphenylsilyloxy)-2-methylpropanal

HRID 1609786노트

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HRID 1609786 반응식
[Si:1]([O:18][CH2:19][C@H:20]([CH3:23])[CH2:21][OH:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1.O>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Si:1]([O:18][CH2:19][C@H:20]([CH3:23])[CH:21]=[O:22])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 117718171-Propanol, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-methyl-, (R)-

생성물 1

HCID 11782372(S)-3-(t-butyldiphenylsilyloxy)-2-methylpropanal수율 97.5%

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

Under argon atmosphere, (R)-3-(t-butyldiphenylsilyloxy)-2-methylpropanol (48) (725 mg, 2.2 mmol) was dissolved in 40 ml of dry dichloromethane. MS-4A (30 mg), NMO (862 mg, 11.1 mmol) and TPAP (catalytic amount) were added to the resultant solution at 0° C., and the mixture was stirred for 15 min. The reaction mixture was further stirred overnight after the temperature was returned to room temperature. Subsequently, H2O was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over magnesium sulfate and evaporated. The obtained crude product was purified by column chromatography (21 g, 4% AcOEt-hexane) to obtain a colorless oily product (49) (700 mg, 97%).

후처리

  1. waitThe reaction mixture was further stirred overnight
  2. customwas returned to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe obtained crude product
  8. customwas purified by column chromatography (21 g, 4% AcOEt-hexane)

출처 및 근거

ORD 기록
ord-90f0904651e848bf81aa9c849b408204
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982257B1

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