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Tetrahydrofuran → Ethyl 2-(2,3-dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)acetate

HRID 2268541
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HRID 2268541 반응식
C(OCC[CH:7]1[CH2:13][CH2:12][C:11]2[C:14]([O:24]C)=[C:15]([O:22][CH3:23])[C:16]([O:20][CH3:21])=[C:17]([O:18]C)[C:10]=2[CH2:9][CH2:8]1)(=O)C.N1C(C(O)=O)=CC=C[C:27]=1[C:35]([OH:37])=[O:36].[CH2:38]1COC[CH2:39]1.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+]>O>[CH3:21][O:20][C:16]1[C:17](=[O:18])[C:10]2[CH2:9][CH2:8][CH:7]([CH2:27][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:13][CH2:12][C:11]=2[C:14](=[O:24])[C:15]=1[O:22][CH3:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183485472-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetate

생성물 1

HCID 18348562Ethyl 2-(2,3-dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)acetate

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

To a mixture of 2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetate (800 mg), 2,6-pyridinedicarboxylic acid (1.14 g), THF (16 ml), and water (8 ml) was dropwise added a solution of CAN (4.98 g) in water (8 ml) with cooling with ice. After the reaction mixture was stirred for 15 min, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=4:1) to yield the entitled compound (604 mg) as an oil.

후처리

  1. temperaturewith cooling with ice
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-e052533e017e4b2799ba4442d4106386
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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