Tetrahydrothiopyran-4-one → 1,1-Dioxo-tetrahydro-thiopyran-4-one

HRID 502294Notes

Reaction equation

HRID 502294 reaction equation
S1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.O[O:9][S:10]([O-:12])=O.[K+].C([O-])(O)=O.[Na+]>CC#N.O>[O:9]=[S:10]1(=[O:12])[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 66173Tetrahydrothiopyran-4-oneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 2622301,1-Dioxo-tetrahydro-thiopyran-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To tetrahydrothiopyran-4-one in CH3CN (50 mL) and H2O (35 mL) at 0° C. was added in portions over 1 hour a mixture of oxone (70.5 g, 115 mmol) and NaHCO3 (29.9 g, 356 mmol). The reaction mixture was then stirred at room temperature for 1 h, diluted in CH3CN (250 mL) and filtered. The filtrate was concentrated, suspended in acetone and filtered. 1,1-Dioxo-tetrahydrothiopyran-4-one (6.3 g, quantitative yield) was obtained as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-227da2d6c97042388e101c7055d586bd
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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