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

HRID 2268542
Notes
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Reaction equation

HRID 2268542 reaction equation
C[O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][OH:16])[CH2:12][CH2:13][C:7]=2[C:6]([O:17]C)=[C:5]([O:19][CH3:20])[C:4]=1[O:21][CH3:22].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>[OH:16][CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][C:8]2[C:3](=[O:2])[C:4]([O:21][CH3:22])=[C:5]([O:19][CH3:20])[C:6](=[O:17])[C:7]=2[CH2:13][CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183486172-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethanol

Product 1

HCID 183485737-(2-Hydroxyethyl)-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione
Yield 66.3%

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)ethanol (800 mg), 2,6-pyridinedicarboxylic acid (1.29 g), THF (16 ml), and water (8 ml) was dropwise added a solution of CAN (5.65 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=2:1) and then with recrystallization from hexane-ethyl acetate to yield the entitled compound (479 mg) 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 silica gel column chromatography (hexane to hexane:ethyl acetate=2:1)
  7. customwith recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a9d5e9e06186454f97180948eaf8d5e7
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