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Acetonitrile → Ethyl 8-(2-ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoate

HRID 2268511
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HRID 2268511 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]([C:36]1([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([O:62][CH2:63][CH3:64])=[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]([O:62][CH2:63][CH3:64])=[O:61])[CH2:37][C:38]2[C:39](=[O:51])[C:40]([O:49][CH3:50])=[C:41]([O:47][CH3:48])[C:42](=[O:45])[C:43]=2[CH2:44]1)=[O:35])[CH3:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348627Ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate

생성물 1

HCID 18348669Ethyl 8-(2-ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoate수율 73.6%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A water (1 ml) solution of CAN (342 mg, 0.624 mmols) was dropwise added to an acetonitrile (2 ml) solution of ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate (100 mg, 0.208 mmols), with cooling with ice. The reaction mixture was stirred for 15 minutes and water was added thereto, 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 only to hexane:ethyl acetate=4:1) to obtain the entitled compound (69 mg) as an oil.

후처리

  1. temperaturewith cooling with ice
  2. extractionwhich was 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 only to hexane

출처 및 근거

ORD 기록
ord-16cbbbfdff9a429d9d88a05952b00d0d
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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