Tetrahydrofuran → HCID 18348544, compound

HRID 2268546Notes

Reaction equation

HRID 2268546 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][CH2:7][CH2:8][CH:9]2[CH2:15][CH2:14][C:13]3[C:16]([O:26]C)=[C:17]([O:24][CH3:25])[C:18]([O:22][CH3:23])=[C:19]([O:20]C)[C:12]=3[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH:9]2[CH2:15][CH2:14][C:13]3[C:16](=[O:26])[C:17]([O:24][CH3:25])=[C:18]([O:22][CH3:23])[C:19](=[O:20])[C:12]=3[CH2:11][CH2:10]2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348662HCID 18348662, compound

Product 1

HCID 18348544HCID 18348544, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a mixture of 7-[2-(4-chlorophenoxy)ethyl]-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene (1.38 g), 2,6-pyridinedicarboxylic acid (1.64 g), THF (52 ml), and water (13 ml) was dropwise added a solution of CAN (7.18 g) in water (13 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 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 alumina column chromatography(ethyl acetate) and then with recrystallization from hexane-ethyl acetate to yield the entitled compound (1.02 g) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. extractionwas extracted 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 alumina column chromatography(ethyl acetate)
  7. customwith recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-407a9b54d0b245af95fcd3e9c7d9b3c7
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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