1-Bromooctane → 5-octyl-2-(4-octyloxyphenyl)pyridine N-oxide

HRID 1780542

Reaktionsgleichung

Reaktionsgleichung von HRID 1780542
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:28][CH:27]=2)=[N:24][CH:25]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(OC1C=CC([Li])=CC=1)CCCCCCC.BrCCCCCCCC>C(Cl)Cl.N1C=CC=CC=1>[CH2:12]([C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:28][CH:27]=2)=[N+:24]([O-:9])[CH:25]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

7

Edukt 4

HCID 81401-BromooctaneHCID 70297m-Chloroperbenzoic acidHCID 3126238Pyridine, 5-octyl-2-[4-(octyloxy)phenyl]-HCID 178506738HCID 178506738, Verbindung

Produkt 1

HCID 543682835-octyl-2-(4-octyloxyphenyl)pyridine N-oxideAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3.03 g (12.3 mmol) of 3-chloroperbenzoic acid in 30 ml of methylene chloride is added dropwise at a temperature of 0° to 5° C. to 3.23 g (8.2 mmol) of 5-octyl-2-(4-octyloxyphenyl)pyridine (prepared, for example, analogously to C. S. Giam, J. Staut, J. Chem. Soc., Chem. Commun. 478 (1970) from pyridine, 4-octyloxyphenyllithium and 1-bromooctane) in 30 ml of methylene chloride. After a reaction time of 3 hours at room temperature, the mixture is washed once with 5% sodium carbonate and twice with sodium chloride solution, the organic phase is dried over sodium sulfate, filtered off, and the solvent is removed by distillation. Purification of the residue by chromatography (silica gel, 8:2 methylene chloride/ethyl acetate) gives 2.20 g of 5-octyl-2-(4-octyloxyphenyl)pyridine N-oxide. ##STR13##

Aufarbeitung

  1. washAfter a reaction time of 3 hours at room temperature, the mixture is washed once with 5% sodium carbonate and twice with sodium chloride solution
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. filtrationfiltered off
  4. customthe solvent is removed by distillation
  5. customPurification of the residue by chromatography (silica gel, 8:2 methylene chloride/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4e58e304ac9a499eb2b7ec70627013d7
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05630962

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