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

HRID 1609786ノート

反応式

HRID 1609786 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-90f0904651e848bf81aa9c849b408204
出典データセット
uspto-grants-2006_01
特許番号
US06982257B1

反応ノート

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