Réaction #339548

Équation de réaction

water

2,6-diiodo-3-methoxy-4-(4-methoxy-butyl)-pyridine

n-butyllithium

ammonium chloride

→

title compound

2-Iodo-5-methoxy-4-(4-methoxy-butyl)-pyridine

Solvants

hexane

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture is warmed to room temperature
2. 2
   Extractionfollowed by extraction with tert-butyl methyl ether (3×)
3. 3
   SéchageThe combined organic layers are dried over sodium sulphate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Mode opératoire

2 mmol of 2,6-diiodo-3-methoxy-4-(4-methoxy-butyl)-pyridine are added to a solution of 4 mmol n-butyllithium in 1.6 ml hexane and 10 ml tetrahydrofuran at −78° C. under an argon atmosphere. The reaction mixture is stirred at −78° C. for 15 minutes. 2 mmol of water are introduced and the reaction mixture is warmed to room temperature. 10% Aqueous ammonium chloride solution is added to the mixture followed by extraction with tert-butyl methyl ether (3×). The combined organic layers are dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and identified based on its Rf value.

Source