m-Chloroperbenzoic acid → (3S)-4-(t-butyldiphenylsilyloxy)-3-methyl-1-butene oxide

HRID 1609788노트

반응식

HRID 1609788 반응식
[Si:1]([O:18][CH2:19][C@@H:20]([CH3:23])[CH:21]=[CH2:22])([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.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>ClCCl>[Si:1]([O:18][CH2:19][C@H:20]([CH3:23])[CH:21]1[O:32][CH2:22]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 16119898(S)-4-(t-butyldiphenylsilyloxy)-3-methyl-1-butene

생성물 1

HCID 10712220(3S)-4-(t-butyldiphenylsilyloxy)-3-methyl-1-butene oxide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Under argon atmosphere, (S)-4-(t-butyldiphenylsilyloxy)-3-methyl-1-butene (50) (1.0 g, 3.1 mmol) was dissolved in 25 ml of dry dichloromethane, mCPBA (1.4 g, 7.4 mmol) was added to the resultant solution at 0° C., and the mixture was stirred for 15 min. Then, the mixture was further stirred overnight after the temperature was returned to room temperature. The reaction mixture was extracted with ethyl acetate after the addition of water. The ethyl acetate layer was washed with brine, dried over magnesium sulfate and evaporated. The obtained crude product was purified by column chromatography (30 g, 2% Et2O-hexane) to obtain a colorless oily product (51). (1.1 g, quant.).

후처리

  1. waitThen, the mixture was further stirred overnight
  2. customwas returned to room temperature
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. additionafter the addition of water
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe obtained crude product
  9. customwas purified by column chromatography (30 g, 2% Et2O-hexane)

출처 및 근거

ORD 기록
ord-a4242bfb7da6413c919bcbb75321134d
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982257B1

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