Tetrahydrofuran → HCID 18348670, compound

HRID 2268540Notes

Reaction equation

HRID 2268540 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][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:30])=[CH:25][CH:24]=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][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[O:30])=[CH:25][CH:24]=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 18348512HCID 18348512, compound

Product 1

HCID 18348670HCID 18348670, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a mixture of 4,5,6,7-tetramethoxy-2-[4-[4-(morpholinocarbonyl)phenoxy]butyl]indan (1.50 g), pyridine-2,6-dicarboxylic acid (1.60 g), THF (30 ml), and water (15 ml) was added an water (15 ml) solution of CAN (7.02 g) with cooling with ice. After being stirred for 15 min, the reaction mixture was diluted with water and 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 recrystallized from ethyl acetate to obtain the entitled compound (965 mg).

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted 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 recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-08e39edd468f4d89b5401dc63ce04959
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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