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

HRID 2268531
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268531
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 98248512-[8-(4-Chlorophenoxy)octyl]-5,6-dimethoxyindan-4,7-dioneAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bc1e6bd238f44327957a68420c5eca30
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326369B1

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