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Tetrahydrofuran → 2,3-Dimethoxy-7-[2-(2-pyridyloxy)ethyl]-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione

HRID 2268551
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HRID 2268551 반응식
C[O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:12][CH2:13][C:7]=2[C:6]([O:23]C)=[C:5]([O:25][CH3:26])[C:4]=1[O:27][CH3:28].N1C(C(O)=O)=CC=CC=1C(O)=O.C1COCC1.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(=O)(O)[O-].[Na+].O>[CH3:28][O:27][C:4]1[C:3](=[O:2])[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:12][CH2:13][C:7]=2[C:6](=[O:23])[C:5]=1[O:25][CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183486022-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]pyridine

생성물 1

HCID 183486222,3-Dimethoxy-7-[2-(2-pyridyloxy)ethyl]-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione수율 75.9%

시약·촉매·용매 2

HCID 962Water용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a mixture of 2-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]pyridine (700 mg), pyridine-2,6-dicarboxylic acid (907 mg), THF (14 ml), and water (7 ml) was added an water (7 ml) solution of CAN (3.97 g) with cooling with ice. After being stirred for 15 min, the reaction mixture was diluted with saturated aqueous sodium bicarbonate and 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=1:2) to obtain the entitled compound (490 mg) as an oil.

후처리

  1. temperaturewith cooling with ice
  2. extractionextracted 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=1:2)

출처 및 근거

ORD 기록
ord-4757479ae84a4f638ee8666e10b285e1
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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