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

HRID 656038ノート

反応式

HRID 656038 の反応式
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

参加物

4

反応物 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

生成物 1

HCID 2875642,2-Dimethyltetrahydro-4h-thiopyran-4-one収率 17.7%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2247acc4f5fb48c5a005586db356f2f6
出典データセット
uspto-grants-2011_12
特許番号
US08071584B2

反応ノート

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