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Tetrahydrofuran → 2-[8-(4-Chlorophenoxy)octyl]-5,6-dimethoxyindan-4,7-dione

HRID 2268531
Notes
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Reaction equation

HRID 2268531 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]2[CH2:23][C:22]3[C:17](=[C:18]([O:30]C)[C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[C:21]=3[O:24]C)[CH2:16]2)=[CH:4][CH:3]=1.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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]2[CH2:16][C:17]3[C:18](=[O:30])[C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[C:21](=[O:24])[C:22]=3[CH2:23]2)=[CH:32][CH:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183485992-[8-(4-Chlorophenoxy)octyl]-4,5,6,7-tetramethoxyindan

Product 1

HCID 98248512-[8-(4-Chlorophenoxy)octyl]-5,6-dimethoxyindan-4,7-dioneYield 50.5%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent3×

Procedure

To a mixture of 2-[8-(4-chlorophenoxy)octyl]-4,5,6,7-tetramethoxyindan (676 mg), 2,6-pyridinedicarboxylic acid (712 mg), THF (14 ml), and water (7 ml) was dropwise added a solution of CAN (3.11 g) in water (7 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=10:1) and then with recrystallization from hexane-diethyl ether to yield the entitled compound (320 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=10:1)
  7. customwith recrystallization from hexane-diethyl ether

Sources & evidence

ORD record
ord-bc1e6bd238f44327957a68420c5eca30
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