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Tetrahydrofuran → 7-[2-(1H-Benzo[d]imidazol-1-yl)ethyl]-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione

HRID 2268548
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HRID 2268548 반응식
C[O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH2:12][CH2:13][C:7]=2[C:6]([O:25]C)=[C:5]([O:27][CH3:28])[C:4]=1[O:29][CH3:30].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>[N:16]1([CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][C:8]3[C:3](=[O:2])[C:4]([O:29][CH3:30])=[C:5]([O:27][CH3:28])[C:6](=[O:25])[C:7]=3[CH2:13][CH2:12]2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[CH:17]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183485591-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1H-benzo[d]imidazole

생성물 1

HCID 183486387-[2-(1H-Benzo[d]imidazol-1-yl)ethyl]-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione
수율 68.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a mixture of 1-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1H-benzo[d]imidazole (380 mg), pyridine-2,6-dicarboxylic acid (465 mg), THF (8 ml), and water (4 ml) was added an water (4 ml) solution of CAN (2.03 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 saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was recrystallized from ethyl acetate to obtain the entitled compound (240 mg).

후처리

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-a676c70f6e6f4b03b556412fc84be02a
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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