Reaction #56488

Reaction equation

Sodium metaperiodate

4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid

→

title compound

4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-1,4-dioxo-2-thiazolidinyl]propyl}benzoic Acid

Solvents

methanol

water

Conditions

Workup

1. 1
   Temperaturewithout further cooling for 16 hours
2. 2
   OtherThe precipitated solid is then removed by filtration
3. 3
   workup.ADDITIONThe filtrate is diluted with water
4. 4
   Extractionextracted with chloroform
5. 5
   ExtractionThe organic extract
6. 6
   Washis washed with brine
7. 7
   Dryingdried over sodium sulfate
8. 8
   Otherevaporated in vacuo
9. 9
   Otherto leave an oily residue which
10. 10
    Otheris chromatographed on silica gel (25 g.)
11. 11
    WashElution with 4% acetic acid in chloroform

Procedure

Sodium metaperiodate (0.75 g., 3.5 mmoles) is added to a cold (0°-5° C.) solution of 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (1.33 g., 3.4 mmoles) in methanol (20 ml.) and water (5 ml.). The resulting mixture is stirred without further cooling for 16 hours. The precipitated solid is then removed by filtration. The filtrate is diluted with water and extracted with chloroform. The organic extract is washed with brine, dried over sodium sulfate, and evaporated in vacuo to leave an oily residue which is chromatographed on silica gel (25 g.). Elution with 4% acetic acid in chloroform affords the title compound as a viscous, yellowish oil.

Source