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

HRID 2268521노트

반응식

HRID 2268521 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e6425c0388a54fa59f61fd1882c2eeef
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326369B1

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