Water → HCID 12137653, compound

HRID 1292783Notes

Reaction equation

HRID 1292783 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:14]=1[CH2:15][S:16][C:17]1[CH2:21][C:20]([CH2:23][CH3:24])([CH3:22])[O:19][N:18]=1.O>C(Cl)(Cl)Cl>[F:12][C:13]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:14]=1[CH2:15][S:16]([C:17]1[CH2:21][C:20]([CH2:23][CH3:24])([CH3:22])[O:19][N:18]=1)=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 12137652HCID 12137652, compound

Product 1

HCID 12137653HCID 12137653, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4.6 g of m-chloroperbenzoic acid (purity: 70%, 18.8 mmoles) was added, with ice-cooling, to a solution of 4.1 g (15.0 mmoles) of 3-(2,6-difluorobenzylthio)-5-ethyl-5-methyl-2-isoxazoline dissolved in 50 ml of chloroform. The mixture was stirred for 1 hour and then at room temperature for 12 hours to give rise to a reaction. After the completion of the reaction the reaction mixture was poured into water, followed by extraction with chloroform. The resulting organic layer was washed with an aqueous sodium hydrogensulfite solution, an aqueous sodium hydrogencarbonate solution, water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 1.5 g (yield: 34.8%) of 3-(2,6-difluorobenzylsulfinyl)-5-ethyl-5-methyl-2-isoxazoline as a white powder (melting point: 30° C. or less).

Workup

  1. customat room temperature for 12 hours to give rise
  2. customto a reaction
  3. customAfter the completion of the reaction the reaction mixture
  4. extractionfollowed by extraction with chloroform
  5. washThe resulting organic layer was washed with an aqueous sodium hydrogensulfite solution
  6. dry with materialan aqueous sodium hydrogencarbonate solution, water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

Sources & evidence

ORD record
ord-ed309cfbea384a71b31aeda677218e0f
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

Loading…