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

HRID 2268512
ノート
印刷プレビュー

反応式

HRID 2268512 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.[C:31]([C:34]1([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59])[CH2:42][C:41]2[C:36](=[C:37]([O:49]C)[C:38]([O:47][CH3:48])=[C:39]([O:45][CH3:46])[C:40]=2[O:43]C)[CH2:35]1)([OH:33])=[O:32]>O>[C:31]([C:34]1([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59])[CH2:42][C:41]2[C:40](=[O:43])[C:39]([O:45][CH3:46])=[C:38]([O:47][CH3:48])[C:37](=[O:49])[C:36]=2[CH2:35]1)([OH:33])=[O:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 183486098-(2-Carboxy-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

生成物 1

HCID 155523518-(2-Carboxy-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoic acid収率 38.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A water (1 ml) solution of CAN (287 mg, 0.523 mmols) was dropwise added to an acetonitrile (2 ml) solution of 8-(2-carboxy-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid (88.6 mg, 0.209 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=1:1 to ethyl acetate only) followed by recrystallization from hexane-ethyl acetate to obtain the entitled compound (32 mg) as crystals.

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
  7. customethyl acetate=1:1 to ethyl acetate only) followed by recrystallization from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-bae2158437e44a5dbc84eff2d7e2157e
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326369B1

反応ノート

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