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Acetonitrile → 4-[4-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)butoxy]phenylmethanol

HRID 2268523
ノート
印刷プレビュー

反応式

HRID 2268523 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[O:32][C:33]1[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[C:39]([O:46]C)=[C:38]2[C:34]=1[CH2:35][CH:36]([CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:58]=[CH:57][C:56]([CH2:59][OH:60])=[CH:55][CH:54]=1)[CH2:37]2>O>[CH3:43][O:42][C:41]1[C:33](=[O:32])[C:34]2[CH2:35][CH:36]([CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]3[CH:58]=[CH:57][C:56]([CH2:59][OH:60])=[CH:55][CH:54]=3)[CH2:37][C:38]=2[C:39](=[O:46])[C:40]=1[O:44][CH3:45]
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 18348611HCID 18348611、化合物

生成物 1

HCID 183486414-[4-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)butoxy]phenylmethanol収率 43.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A water (1.0 ml) solution of CAN (1.24 g, 2.27 mmols) was dropwise added to an acetonitrile (8.0 ml) solution of 4-[4-(4,5,6,7-tetramethoxyindan-2-yl)butoxy]phenylmethanol (370 mg, 0.888 mmols), with cooling with ice, and 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 water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 2:1) followed by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (150 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 water
  4. dry with materiala saturated aqueous sodium chloride solution, and then dried
  5. customThe solvent was evaporated out in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 2:1)
  7. customfollowed by recrystallization (from hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-67ce911d53884dc8bc4add837e3d6d1b
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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