Acetonitrile → Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-5,6-dimethoxy-4,7-dioxo-2-indancarboxylate

HRID 2268521ノート

反応式

HRID 2268521 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]([CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2([C:63]([O:65][CH2:66][CH3:67])=[O:64])[CH2:54][C:53]3[C:48](=[C:49]([O:61]C)[C:50]([O:59][CH3:60])=[C:51]([O:57][CH3:58])[C:52]=3[O:55]C)[CH2:47]2)=[CH:42][CH:41]=1)=[O:35])[CH3:32]>O>[CH2:31]([O:33][C:34]([CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2([C:63]([O:65][CH2:66][CH3:67])=[O:64])[CH2:54][C:53]3[C:52](=[O:55])[C:51]([O:57][CH3:58])=[C:50]([O:59][CH3:60])[C:49](=[O:61])[C:48]=3[CH2:47]2)=[CH:42][CH:41]=1)=[O:35])[CH3:32]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348634Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylate

生成物 1

HCID 15552354Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-5,6-dimethoxy-4,7-dioxo-2-indancarboxylate収率 70.8%

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 (795 mg, 1.45 mmols) was dropwise added to an acetonitrile (6.0 ml) solution of ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylate (300 mg, 0.581 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 in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to obtain the entitled compound (200 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 water
  4. dry with materiala saturated aqueous sodium chloride solution and then dried
  5. customThe solvent was evaporated in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

出典と根拠

ORDレコード
ord-e6425c0388a54fa59f61fd1882c2eeef
出典データセット
uspto-grants-2001_12
特許番号
US06326369B1

反応ノート

読み込み中…