HCID 18319142, compound → HCID 18319072, compound

HRID 1700932Notes

Reaction equation

HRID 1700932 reaction equation
[CH2:1]([S:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].I([O-])(=O)(=O)=[O:32].[Na+]>CO.O>[CH2:1]([S:13]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=[O:30])[C:26]([F:27])([F:28])[F:29])=[CH:19][CH:18]=1)=[O:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 18319142HCID 18319142, compoundHCID 23667635Sodium periodate

Product 1

HCID 18319072HCID 18319072, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

A solution of 4-[4-[2-(dodecylthio)ethoxy]phenyl]-1,1,1-trifluoro-2-butanone (0.340 g, 0.76 mmol) in methanol (15 ml) was treated with a solution of sodium periodate (0.165 g, 0.77 mmol) in water (3 ml) and the resulting mixture was stirred at 22° C. for 18 h. The solid formed was filtered and washed with methanol. This filtrate was then concentrated under reduced pressure and then partitioned between water and ethyl acetate. The organic phase was then dried (magnesium sulfate) and concentrated. The residue was chromatographed on silica gel (elution toluene-ethyl acetate 1:1) to give 0.335 g (90%) of 4-[4-[2-(dodecylsulfinyl)ethoxy]phenyl]-1,1,1-trifluoro-2-butanone as a white solid. By 1HNMR this product was a 6:4 mixture of trifluoromethyl ketone and hydrated trifluoromethyl ketone. The pure hydrate precipitates from ethyl acetate-hexane: m.p. 98-100° C.

Workup

  1. customThe solid formed
  2. filtrationwas filtered
  3. washwashed with methanol
  4. concentrationThis filtrate was then concentrated under reduced pressure
  5. custompartitioned between water and ethyl acetate
  6. dry with materialThe organic phase was then dried (magnesium sulfate)
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel (elution toluene-ethyl acetate 1:1)

Sources & evidence

ORD record
ord-b281521704e34092adf609f15061d3e6
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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