m-Chloroperbenzoic acid → 2-(3,4,4-Trifluoro-3-butenylsulfinyl)oxazole

HRID 351793Notes

Reaction equation

HRID 351793 reaction equation
[F:1][C:2](=[C:11]([F:13])[F:12])[CH2:3][CH2:4][S:5][C:6]1[O:7][CH:8]=[CH:9][N:10]=1.ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCl>[F:1][C:2](=[C:11]([F:12])[F:13])[CH2:3][CH2:4][S:5]([C:6]1[O:7][CH:8]=[CH:9][N:10]=1)=[O:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 129939582-(3,4,4-Trifluoro-3-butenylthio)oxazole

Product 1

HCID 129939592-(3,4,4-Trifluoro-3-butenylsulfinyl)oxazoleYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 g of 2-(3,4,4-trifluoro-3-butenylthio)oxazole and 1.5 g of m-chloroperbenzoic acid (purity about 70%) were added to 50 ml of dichloromethane and stirred at room temperature for 20 hours. The reaction mixture was washed with 50 ml of 1N aqueous solution of sodium hydroxide and dried with magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography (eluent: ethyl acetate:dichloromethane=1:4) to obtain 1.0 g of 2-(3,4,4-trifluoro-3-butenylsulfinyl)oxazole as colorless oil (yield 92.9%, n20D=1.4820).

Workup

  1. washThe reaction mixture was washed with 50 ml of 1N aqueous solution of sodium hydroxide
  2. dry with materialdried with magnesium sulfate
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography (eluent: ethyl acetate:dichloromethane=1:4)

Sources & evidence

ORD record
ord-bf31b3bd74f54c4e8c75f7126a5cb0f5
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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