Methanesulfonic Acid → HCID 19370791, compound

HRID 129932Notes

Reaction equation

HRID 129932 reaction equation
S1C[CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH:8](OC)(OC)OC.[CH3:15][S:16]([OH:19])(=O)=[O:17]>CO.C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:8][O:7][C:4]1[CH2:5][CH2:15][S:16](=[O:19])(=[O:17])[CH2:2][CH:3]=1

Participants

7

Reactant 3

HCID 6395Methanesulfonic AcidHCID 9005Trimethyl orthoformateHCID 66173Tetrahydrothiopyran-4-one

Product 1

HCID 19370791HCID 19370791, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-1,1-dioxo-5,6-dihydro-(2H)-Thiopyran is prepared from the available tetrahydrothiopyran-4-one (Aldrich) by ketalization with trimethyl orthoformate in methanol containing catalytic sulfuric acid, followed by oxidation with excess m-chlorolperbenzoic acid in methylene chloride, followed by acid promoted elimination of methanol using, for instance, methanesulfonic acid in hot chloroform (to drive off by-product methanol by distillation).

Sources & evidence

ORD record
ord-8518074d808c40b68083e466d7b1db47
Source dataset
uspto-grants-1995_11
Patent number
US05470974

Reaction notes

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