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

HRID 1609788Notes

Reaction equation

HRID 1609788 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  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)

Sources & evidence

ORD record
ord-a4242bfb7da6413c919bcbb75321134d
Source dataset
uspto-grants-2006_01
Patent number
US06982257B1

Reaction notes

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