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

HRID 2268551Notes

Reaction equation

HRID 2268551 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: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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4757479ae84a4f638ee8666e10b285e1
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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