Reacción #473057

Ecuación de reacción

Sodium hydride

Tetrahydro-2H-thiopyran-4-ol

2-Bromo-6-(bromomethyl)pyridine

→

title compound

2-Bromo-6-[(tetrahydro-2H-thiopyran-4-yloxy)methyl]pyridine

Disolventes

tetrahydrofuran

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction was warmed to and
2. 2
   Temperaturamaintained at ambient temperature overnight
3. 3
   Otroquenched slowly with water
4. 4
   Otrothe layers were separated
5. 5
   Extracciónthe aqueous layer was extracted with ethyl acetate
6. 6
   SecadoThe combined organic layers were dried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe crude mixture was purified by silica gel chromatography

Procedimiento

Sodium hydride (0.24 g, 5.98 mmol) was suspended in tetrahydrofuran (19.9 mL) and cooled to 0° C. Tetrahydro-2H-thiopyran-4-ol (0.24 g, 1.99 mmol) was added and the reaction was stirred for 30 minutes. 2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (0.5 g, 1.99 mmol) was added and the reaction was warmed to and maintained at ambient temperature overnight. The reaction was diluted with ethyl acetate, quenched slowly with water, the layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

Fuente