Hexane → HCID 22033402, compound

HRID 1792332Notes

Reaction equation

HRID 1792332 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH2:9][CH2:10][CH2:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14].I([O-])(=O)(=O)=[O:22].[Na+].CCCCCC.C(OCC)(=O)C>CO.O>[CH3:20][O:19][CH:3]([O:2][CH3:1])[CH2:4][CH2:5][CH2:6][CH2:7][S:8]([CH2:9][CH2:10][CH2:11][C:12]([F:17])([F:18])[C:13]([F:16])([F:14])[F:15])=[O:22]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 220330545,5-Dimethoxy-1-(4,4,5,5,5-pentafluoropentylthio)pentaneHCID 23667635Sodium periodate

Product 1

HCID 22033402HCID 22033402, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of 5,5-dimethoxy-1-(4,4,5,5,5-pentafluoropentylthio)pentane (460 mg, 1.4 mmol) in methanol (10 mg) were added sodium periodate (420 mg, 2.0 mmol) dissolved in water (8 ml) and methanol (5 ml), and the resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=2:1) to give 5,5-dimethoxy-1-(4,4,5,5,5-pentafluoropentylsulfinyl)pentane (365 mg, yield 76%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customThis crude product thus obtained

Sources & evidence

ORD record
ord-e4a8560b4fb846be894ecde8d8827abe
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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