Acetonitrile → 8-(2-Ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoic acid

HRID 2268513ノート

反応式

HRID 2268513 の反応式
O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C(#N)C.[CH2:31]([O:33][C:34]([C:36]1([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([OH:62])=[O:61])[CH2:44][C:43]2[C:38](=[C:39]([O:51]C)[C:40]([O:49][CH3:50])=[C:41]([O:47][CH3:48])[C:42]=2[O:45]C)[CH2:37]1)=[O:35])[CH3:32]>O>[CH2:31]([O:33][C:34]([C:36]1([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([OH:62])=[O:61])[CH2:44][C:43]2[C:42](=[O:45])[C:41]([O:47][CH3:48])=[C:40]([O:49][CH3:50])[C:39](=[O:51])[C:38]=2[CH2:37]1)=[O:35])[CH3:32]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 183486378-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

生成物 1

HCID 155523508-(2-Ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoic acid収率 68%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A water (1 ml) solution of CAN (238 mg, 0.435 mmols) was dropwise added to an acetonitrile (2 ml) solution of 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid (78.6 mg, 0.174 mmols) with cooling with ice and then stirring was continued for 15 minutes. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried. The solvent was evaporated in vacuo and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to ethyl acetate only) to obtain the entitled compound (50 mg) as an oil.

後処理

  1. temperaturewith cooling with ice
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. customdried
  5. customThe solvent was evaporated in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane

出典と根拠

ORDレコード
ord-f3335647d96e453a83c0ed9c7a7eee4e
出典データセット
uspto-grants-2001_12
特許番号
US06326369B1

反応ノート

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