Reaction #417948

Reaction equation

2-bromo-5-hydroxypyridine

1-bromopropane

K2CO3

→

2-Bromo-5-propoxy-pyridine

Solvents

ACN

Conditions

Workup

1. 1
   Temperatureat reflux over night
2. 2
   OtherAfterwards the reaction is quenched by the addition of water
3. 3
   Extractionextracted with TBME
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Otherthe solvent is removed in vacuo
7. 7
   OtherThe crude product is purified by column chromatography (silica gel, PE/EtOAc)

Procedure

10.0 g (57.5 mmol) 2-bromo-5-hydroxypyridine, 28.3 g (230 mmol) 1-bromopropane and 19.9 g (143.7 mmol) K2CO3 are added to 1 L ACN and stirred at reflux over night. Afterwards the reaction is quenched by the addition of water and extracted with TBME. The org. layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc).

Source