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 2268545Notes

Reaction equation

HRID 2268545 reaction equation
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]

Participants

6

Reactant 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

Product 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 acidYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7270509900a14d539a76243c81853ee8
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…