2,2-Dimethyl-4-oxo-tetrahydro-thiopyran-3-carboxylic acid methyl ester → 2,2-Dimethyltetrahydro-4h-thiopyran-4-one

HRID 656038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656038
COC([CH:5]1[C:10](=[O:11])[CH2:9][C:8]([CH3:13])([CH3:12])[S:7][CH2:6]1)=O.COC(C1C(=O)CCSC1(C)C)=O>OS(O)(=O)=O>[CH3:12][C:8]1([CH3:13])[CH2:9][C:10](=[O:11])[CH2:5][CH2:6][S:7]1

Komponenten

4

Edukt 2

HCID 593326592,2-Dimethyl-4-oxo-tetrahydro-thiopyran-3-carboxylic acid methyl esterHCID 593327336,6-Dimethyl-4-oxo-tetrahydro-thiopyran-3-carboxylic acid methyl ester

Produkt 1

HCID 2875642,2-Dimethyltetrahydro-4h-thiopyran-4-oneAusbeute 17,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

The mixture of 6,6-Dimethyl-4-oxo-tetrahydro-thiopyran-3-carboxylic acid methyl ester and 2,2-Dimethyl-4-oxo-tetrahydro-thiopyran-3-carboxylic acid methyl ester (42 g) in 10% aq. H2SO4 solution (1000 mL) was heated at reflux for 70 h. Then the mixture was extracted with Et2O (3×300 mL), the combined organic layer was washed with sat. NaHCO3 (120 mL) and brine (120 mL), dried over Na2SO4 and evaporated under vacuum to give the title compound as a white solid (5.3 g, 17.7%, two steps).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 70 h
  3. extractionThen the mixture was extracted with Et2O (3×300 mL)
  4. washthe combined organic layer was washed with sat. NaHCO3 (120 mL) and brine (120 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2247acc4f5fb48c5a005586db356f2f6
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071584B2

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