Water → HCID 58026162, compound

HRID 2387304Notes

Reaction equation

HRID 2387304 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3](=[O:16])[CH2:4][C:5]([CH3:15])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][CH3:14])[CH3:6].[OH2:19].I([O-])(=O)(=O)=[O:21].[Na+]>C(#N)C.C(OCC)C.[Ru](Cl)(Cl)Cl>[F:18][C:2]([F:1])([F:17])[C:3](=[O:16])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([CH3:14])(=[O:21])=[O:19])([CH3:6])[CH3:15]

Participants

7

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 58026148HCID 58026148, compound

Product 1

HCID 58026162HCID 58026162, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1,1,1-Trifluoro-4-methyl-4-(2-methylsulfanylphenyl)pentan-2-one (21.0 g, 60.8 mmol) was dissolved in 240 mL of acetonitrile. 80 mL of water was added followed by sodium metaperiodate (44.9 g, 210 mmol) and ruthenium (III) chloride (0.622 g, 3.0 mmol). The resulting reaction was stirred for 18 hours. The reaction mixture was diluted with 500 mL of diethyl ether (Et2O) and the layers were mixed and separated. The aqueous was washed with 500 mL of diethyl ether and the organics were combined, dried over sodium sulfate (Na2SO4), decanted, and concentrated in vacuo to a thick orange oil. The crude material was separated by flash column chromatography with 0-35% EtOAc/hexanes as the eluent. 1,1,1-Trifluoro-4-(2-methanesulfonylphenyl)-4-methylpentan-2-one (16.9 g, 90%) was obtained as a colorless oil.

Workup

  1. customThe resulting reaction
  2. additionthe layers were mixed
  3. customseparated
  4. washThe aqueous was washed with 500 mL of diethyl ether
  5. dry with materialdried over sodium sulfate (Na2SO4)
  6. customdecanted
  7. concentrationconcentrated in vacuo to a thick orange oil
  8. customThe crude material was separated by flash column chromatography with 0-35% EtOAc/hexanes as the eluent

Sources & evidence

ORD record
ord-8d878618ea364343bfce5208aa11568b
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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