Tetrahydrofuran → 4-[3-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)propoxy]benzoic acid

HRID 2268532Notes

Reaction equation

HRID 2268532 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][CH:6]([CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=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>[CH3:13][O:12][C:11]1[C:3](=[O:2])[C:4]2[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:29][CH:30]=3)[CH2:7][C:8]=2[C:9](=[O:16])[C:10]=1[O:14][CH3:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183485514-[3-(4,5,6,7-Tetramethoxyindan-2-yl)propoxy]benzoic acid

Product 1

HCID 183486594-[3-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)propoxy]benzoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a mixture of 4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzoic acid (1.20 g), 2,6-pyridinedicarboxylic acid (1.44 g), THF (24 ml), and water (12 ml) was dropwise added a solution of CAN (6.30 g) in water (12 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 (ethyl acetate) and then with recrystallization from ethyl acetate to yield the entitled compound (868 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 (ethyl acetate)
  7. customwith recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-28d46648feac4d6cb829d158a917add4
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…