Tetrahydrofuran → 4-[2-(2,3-Dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid

HRID 2268545노트

반응식

HRID 2268545 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:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH2:12][CH2:13][C:7]=2[C:6]([O:26]C)=[C:5]([O:28][CH3:29])[C:4]=1[O:30][CH3:31].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+]>O>[CH3:29][O:28][C:5]1[C:6](=[O:26])[C:7]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:24][CH:25]=3)[CH2:10][CH2:9][C:8]=2[C:3](=[O:2])[C:4]=1[O:30][CH3:31]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183486524-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid

생성물 1

HCID 183485244-[2-(2,3-Dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid수율 43%

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

To a mixture of 4-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid (1.00 g), 2,6-pyridinedicarboxylic acid (1.16 g), THF (40 ml), and water (10 ml) was dropwise added a solution of CAN (5.09 g) in water (10 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 combined solvent of ethyl acetate and THF. The organic layer was washed with water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was recrystallized from THF-ethyl acetate to yield the entitled compound (400 mg) as crystals.

후처리

  1. temperaturewith cooling with ice
  2. extractionwas extracted with combined solvent of ethyl acetate and THF
  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 recrystallized from THF-ethyl acetate

출처 및 근거

ORD 기록
ord-7270509900a14d539a76243c81853ee8
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326369B1

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