Tetrahydrofuran → HCID 18348552, compound

HRID 2268543Notes

Reaction equation

HRID 2268543 reaction equation
C[O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:12][CH2:13][C:7]=2[C:6]([O:18]C)=[C:5]([O:20][CH3:21])[C:4]=1[O:22][CH3:23].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>[CH3:23][O:22][C:4]1[C:3](=[O:2])[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:12][CH2:13][C:7]=2[C:6](=[O:18])[C:5]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348593HCID 18348593, compound

Product 1

HCID 18348552HCID 18348552, compoundYield 62%

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)acetic acid (800 mg), 2,6-pyridinedicarboxylic acid (1.24 g), THF (16 ml), and water (8 ml) was dropwise added a solution of CAN (5.42 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, 1N hydrochloric acid, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was recrystallized from ethyl acetate to yield the entitled compound (450 mg) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with, 1N hydrochloric acid, water, and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-990a3f56a15b4c8a97a8e0cc85d492d6
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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