HCID 22483913, compound → HCID 22483918, compound

HRID 2180902Notes

Reaction equation

HRID 2180902 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([S:9][CH3:10])[C:5]=2[C:11]([C:13]2[C:14]([CH3:23])=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)=[O:12])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:25].[Na+]>CC(C)=O.O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([S:9]([CH3:10])=[O:25])[C:5]=2[C:11]([C:13]2[C:14]([CH3:23])=[N:15][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:17][CH:18]=2)=[O:12])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 22483913HCID 22483913, compoundHCID 23667635Sodium periodate

Product 1

HCID 22483918HCID 22483918, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

1.50 g (0.0043 mol) of (5-cyclopropyl-3-methylsulfanyi-isoxazol-4-yl)-(2-methyl-6-trifluoromethyl-pyridin-3-yl)-methanone are dissolved in 30 ml of acetone/water (2:1 mixture) and 1.02 g (0.0048 mol) of sodium metaperiodate are added in portions at 22° C. After 5 hours, the reaction mixture is concentrated by evaporation using a rotary evaporator. The residue is taken up in water and ethyl acetate. The ethyl acetate phase is dried over sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel (eluant: ethyl acetate/hexane 3/1). 0.8 g (51%) of the desired product is obtained in the form of white crystals (m.p. 96-97° C.).

Workup

  1. concentrationthe reaction mixture is concentrated by evaporation
  2. customa rotary evaporator
  3. dry with materialThe ethyl acetate phase is dried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel (eluant: ethyl acetate/hexane 3/1)

Sources & evidence

ORD record
ord-632fd48b2579435396fe660b361f0dc8
Source dataset
uspto-grants-2005_05
Patent number
US06890885B2

Reaction notes

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