EDTA disodium salt → 1,1-Dioxo-tetrahydro-thiopyran-4-one

HRID 2363975Notes

Reaction equation

HRID 2363975 reaction equation
S1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+].O[O:36][S:37]([O-:39])=O.[K+]>C(#N)C.ClCCl>[S:37]1(=[O:39])(=[O:36])[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8759EDTA disodium saltHCID 66173Tetrahydrothiopyran-4-oneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 2622301,1-Dioxo-tetrahydro-thiopyran-4-oneYield 64.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tetrahydrothiopyran-4-one (0.400 g, 3.40 mmol) in acetonitrile (4.5 mL) was added Na2EDTA (3 mL, 0.0004 M in water). Solid NaHCO3 (2.70 g, 32.0 mmol) and OXONE (trade name, 6.30 g, 10.3 mmol) were combined separately and this dry mixture was added to the reaction mixture over 30 min. Then, the reaction was allowed to stir for 50 min. The mixture was diluted with dichloromethane (80 mL) and the white inorganic material was removed by filtration. The filtrate was dried over magnesium sulfate and concentrated to give the title compound (0.326 g, 64%) as a white solid:

Workup

  1. additionthis dry mixture was added to the reaction mixture over 30 min
  2. customthe white inorganic material was removed by filtration
  3. dry with materialThe filtrate was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fabe9ed61d084f79a0d47182e6d995db
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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