Réaction #1103

Équation de réaction

water

benzyltriphenylphosphonium bromide

butyllithium

4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine

→

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

Solvants

hexane

DMSO

ethylene glycol dimethyl ether

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source