Tetrahydrothiopyran-4-one-3-carboxylic acid → 2,3-Dihydrothiopyran-4-one-3-carboxylic acid

HRID 841888Notes

Reaction equation

HRID 841888 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH:3]([C:8]([OH:10])=[O:9])[CH2:2]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[S:1]1[CH:6]=[CH:5][C:4](=[O:7])[CH:3]([C:8]([OH:10])=[O:9])[CH2:2]1

Participants

4

Reactant 1

HCID 22617731Tetrahydrothiopyran-4-one-3-carboxylic acid

Product 1

HCID 226177402,3-Dihydrothiopyran-4-one-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of tetrahydrothiopyran-4-one-3-carboxylic acid, allyl ester (Example 4, step A) (2.3 g, 11.5 mmol) in 100 mL dry chloroform at room temperature was added activated manganese dioxide (10 g, 115 mmol) and the resulting mixture was refluxed for 5 h. The reaction mixture was filtered and evaporated. The the remaining residue was purified by flash column chromatography on silica gel eluted with hexane:ethyl acetate (7:3) to give 2,3-dihydrothiopyran-4-one-3-carboxylic acid, allyl ester (0.988 g).

Workup

  1. temperaturethe resulting mixture was refluxed for 5 h
  2. filtrationThe reaction mixture was filtered
  3. customevaporated
  4. customThe the remaining residue was purified by flash column chromatography on silica gel
  5. washeluted with hexane:ethyl acetate (7:3)

Sources & evidence

ORD record
ord-e92aeb42ebb44e6aaf12f44025911ec5
Source dataset
uspto-grants-2002_04
Patent number
US06372733B1

Reaction notes

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