Water → 4-(4-Benzylidenecyclohexylamino)-3-methoxy-2-methylpyridine

HRID 1007

Reaktionsgleichung

Reaktionsgleichung von HRID 1007
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.O=[C:34]1[CH2:39][CH2:38][CH:37]([NH:40][C:41]2[CH:46]=[CH:45][N:44]=[C:43]([CH3:47])[C:42]=2[O:48][CH3:49])[CH2:36][CH2:35]1.O>COCCOC.CCCCCC.CS(C)=O>[CH:2](=[C:34]1[CH2:39][CH2:38][CH:37]([NH:40][C:41]2[CH:46]=[CH:45][N:44]=[C:43]([CH3:47])[C:42]=2[O:48][CH3:49])[CH2:36][CH2:35]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 2734970Benzyltriphenylphosphonium bromideHCID 196939514-(4-Oxocyclohexylamino)-3-methoxy-2-methylpyridineHCID 178418339Butyllithium

Produkt 1

HCID 196939574-(4-Benzylidenecyclohexylamino)-3-methoxy-2-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8058HexaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

7.8 g of benzyltriphenylphosphonium bromide in 50 ml of ethylene glycol dimethyl ether are deprotonated at 10° to 20° C. using 11 ml of 1.6 molar butyllithium solution in hexane. After 30 minutes 1.3 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine are added dropwise in 10 ml of DMSO. After 5 hours at 40° to 50° C. the mixture is poured into water and extracted with methylene chloride. The product is purified by column chromatography on silica gel (eluent: ethanol). 0.6=41%; m.p.: 120° C.

Aufarbeitung

  1. customare deprotonated at 10° to 20° C.
  2. extractionextracted with methylene chloride
  3. customThe product is purified by column chromatography on silica gel (eluent: ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-13d9fefea0ad416fb3ed3b3104651c13
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723450

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