Tetrahydrofuran → HCID 18348682, compound

HRID 2268538Notes

Reaction equation

HRID 2268538 reaction equation
C[O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16]C)=[C:8]2[C:4]=1[CH2:5][C:6]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7]2.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:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:6]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:5][C:4]2[C:3](=[O:2])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9](=[O:16])[C:8]=2[CH2:7]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348532HCID 18348532, compound

Product 1

HCID 18348682HCID 18348682, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 8-(4,5,6,7-tetramethoxy-2-phenylindan-2-yl)octanol (1.00 g), 2,6-pyridinedicarboxylic acid (1.13 g), THF (20 ml), and water (10 ml) was dropwise added a solution of CAN (4.92 g) in water (10 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 (542 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-2f54b83c6f2c4ece8388708bbbfd4aff
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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