Selenium Dioxide → 6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 17874

反応式

HRID 17874 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([OH:21])[CH:9]=2)=[O:5])[CH3:2].[Se](=O)=[O:23]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([OH:21])[CH:9]=2)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 24007Selenium DioxideHCID 118452786-hydroxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

生成物 1

HCID 118452796-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester収率 58%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

6-Hydroxy-3-phenyl-1H-indene-2-carboxylate ethyl ester (1 g, 3.57 mmol) was dissolved in 1,4-dioxane (50 ml), and then selenium dioxide (5.49 g, 53.55 mmol) was added thereto. The mixture was refluxed for 12 hour with vigorous stirring. The resulting mixture was filtered and concentrated, and the concentrate was extracted with ethyl acetate. The extract was washed with brine, and the organic layer was dried over anhydrous magnesium sulfate, concentrated under a reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain the title compound (58%) as a rich red solid.

後処理

  1. temperatureThe mixture was refluxed for 12 hour with vigorous stirring
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated
  4. extractionthe concentrate was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

出典と根拠

ORDレコード
ord-9317969a1a364c05ade6516d6d0ab071
出典データセット
uspto-grants-2010_06
特許番号
US07741323B2

関連ノート

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