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 2268545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268545
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]

Komponenten

6

Edukt 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

Produkt 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 acidAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7270509900a14d539a76243c81853ee8
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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