Sodium periodate → 6-Benzenesulfinyl-hexa-2,4-dienoic acid methyl ester

HRID 2245763Notes

Reaction equation

HRID 2245763 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I([O-])(=O)(=O)=[O:18].[Na+]>CO.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][S:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:18]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 730968226-Phenylsulfanyl-hexa-2,4-dienoic acid methyl ester

Product 1

HCID 851002856-Benzenesulfinyl-hexa-2,4-dienoic acid methyl esterYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 6-phenylsulfanyl-hexa-2,4-dienoic acid methyl ester (0.336 g, 1.43 mmol) in methanol (17 mL) was added dropwise at 0° C. a solution of sodium metaperiodate (0.37 g, 1.72 mmol) in distilled water (6 mL). The mixture was allowed to warm to 20° C. and 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) and then brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (1:2 to 1:1 to 2:1 ethyl acetate:60-80 ° C. petroleum ether). The resulting powder was recrystallised from diethyl ether to give the title compound (0.29 g, 81%) as a white solid, mp 82-84° C.

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 dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give an oil that
  11. customwas purified by flash chromatography (1:2 to 1:1 to 2:1 ethyl acetate:60-80 ° C. petroleum ether)
  12. customThe resulting powder was recrystallised from diethyl ether

Sources & evidence

ORD record
ord-fef6b23d23244f1eaf0342044a73f4e0
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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