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Tetrahydrofuran → Ethyl 2-(2,3-dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)acetate

HRID 2268541
Notes
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Reaction equation

HRID 2268541 reaction equation
C(OCC[CH:7]1[CH2:13][CH2:12][C:11]2[C:14]([O:24]C)=[C:15]([O:22][CH3:23])[C:16]([O:20][CH3:21])=[C:17]([O:18]C)[C:10]=2[CH2:9][CH2:8]1)(=O)C.N1C(C(O)=O)=CC=C[C:27]=1[C:35]([OH:37])=[O:36].[CH2:38]1COC[CH2:39]1.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>[CH3:21][O:20][C:16]1[C:17](=[O:18])[C:10]2[CH2:9][CH2:8][CH:7]([CH2:27][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:13][CH2:12][C:11]=2[C:14](=[O:24])[C:15]=1[O:22][CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183485472-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetate

Product 1

HCID 18348562Ethyl 2-(2,3-dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a mixture of 2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetate (800 mg), 2,6-pyridinedicarboxylic acid (1.14 g), THF (16 ml), and water (8 ml) was dropwise added a solution of CAN (4.98 g) in water (8 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 silica gel column chromatography (hexane to hexane:ethyl acetate=4:1) to yield the entitled compound (604 mg) as an oil.

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 silica gel column chromatography (hexane to hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-e052533e017e4b2799ba4442d4106386
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326369B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes