Reaction #66120

Reaction equation

2-hydroxy-4,6-dimethylpyridine

potassium carbonate

1-(2-bromo-ethoxy)-4-nitro-benzene

→

2,4-dimethyl-6-[2-(4-nitro-phenoxy)-ethoxy]-pyridine

Yield 13.3%

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturemaintained for 15 h
2. 2
   TemperatureThe mixture was cooled to ambient temperature
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   Otherto give a residue which
6. 6
   Otherwas purified by column chromatography

Procedure

A mixture of 2-hydroxy-4,6-dimethylpyridine (1.7 g, 13.8 mmol), potassium carbonate (3.82 g, 27.6 mmol) and 1-(2-bromo-ethoxy)-4-nitro-benzene (4.0 g, 16.6 mmol) in DMF (30 mL) was heated to 120° C. and maintained for 15 h. The mixture was cooled to ambient temperature, filtered and concentrated to give a residue which was purified by column chromatography using 4% ethyl acetate/petroleum ether as eluent to afford 2,4-dimethyl-6-[2-(4-nitro-phenoxy)-ethoxy]-pyridine as yellow solid (530 mg, 11%).

Source