Sodium periodate → 6-(4-Chlorobenzenesulfinyl)-hexa-2,4-dienoic acid methyl ester

HRID 2245764Notes

Reaction equation

HRID 2245764 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.I([O-])(=O)(=O)=[O:19].[Na+]>CO.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:17])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][S:9]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:19]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 859734646-(4-Chlorophenylsulfanyl)-hexa-2,4-dienoic acid methyl ester

Product 1

HCID 850936646-(4-Chlorobenzenesulfinyl)-hexa-2,4-dienoic acid methyl esterYield 77%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 6-(4-chlorophenylsulfanyl)-hexa-2,4-dienoic acid methyl ester (0.396 g, 1.47 mmol) in methanol (20 mL) was added dropwise at 0° C. a solution of sodium metaperiodate (0.37 g, 1.72 mmol) in distilled water (10 mL). The mixture was allowed to warm to 20° C., then heated at reflux for 5 hours. The solution was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (20 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (10 mL), distilled water (10 mL), then with brine. The organic layer was then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (2:8 ethyl acetate:40-60° C. petroleum ether). The resulting powder was recrystallised from ethylacetate/40-60° C. petroleum ether to give the title compound (0.32 g, 77%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. concentrationThe solution was concentrated under reduced pressure
  4. customto give an oil that
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (10 mL)
  6. distillationdistilled water (10 mL)
  7. dry with materialThe organic layer was then dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give an oil that
  11. customwas purified by flash chromatography (2:8 ethyl acetate:40-60° C. petroleum ether)
  12. customThe resulting powder was recrystallised from ethylacetate/40-60° C. petroleum ether

Sources & evidence

ORD record
ord-4d78ab838b444c3dac6027ded84a25d4
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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