Reacción #663848

Ecuación de reacción

3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate

ammonium chloride

sodium hydride

5-bromo-2-hydroxy-6-methylpyridine

3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate

Sodium hydride

→

title compound

Rendimiento 89.2%

4-(5-bromo-6-methylpyridin-2-yloxy)-2-methylbutan-2-ol

Rendimiento 89.2%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Otrothe resultant reaction mixture
3. 3
   Otrothe resultant reaction mixture
4. 4
   workup.STIRRINGwas stirred at 60° C. for 1.5 hours
5. 5
   workup.ADDITIONwas further added
6. 6
   Extracciónthe mixture was extracted with ethyl acetate
7. 7
   LavadoThe organic phase was washed with brine
8. 8
   Secadodried over anhydrous sodium sulfate
9. 9
   OtroFrom the organic phase, the solvent was removed by evaporation under reduced pressure
10. 10
    Otrothe resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=50:50 to 33:67)

Procedimiento

To a suspension of sodium hydride (containing about 40% of a mineral oil, 0.38 g) in N,N-dimethylformamide (10 mL), 5-bromo-2-hydroxy-6-methylpyridine (1.00 g) and 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (1.51 g) were added under ice-cooling and the resultant reaction mixture was stirred at 60° C. for 2.5 hours. To the mixture, 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (0.50 g) was further added and the resultant reaction mixture was stirred at 60° C. for 1.5 hours. Sodium hydride (containing about 40% of a mineral oil, 40 mg) was further added. To the reaction mixture, a saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and then dried over anhydrous sodium sulfate. From the organic phase, the solvent was removed by evaporation under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=50:50 to 33:67) to give the title compound (1.3 g) as a pale yellow oil.

Fuente