Reacción #48290

Ecuación de reacción

sodium bicarbonate

chloro(methoxy)methane

6-bromopyridin-3-ol

NaH

→

title compound

2-bromo-5-(methoxymethoxy)pyridine

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction stirred an additional 1 h at 0° C
2. 2
   workup.STIRRINGthe suspension stirred 30 min
3. 3
   ExtracciónThe solution was extracted with EtOAc (3×400 mL)
4. 4
   Lavadothe combined organic layers washed with H2O (500 mL), saturated NaCl (500 mL)
5. 5
   Secadodried (Na2SO4)
6. 6
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of 6-bromopyridin-3-ol (25 g, 144 mmol) in DMF (300 mL) at 0° C. under N2 is added portionwise NaH (5.7 g, 144 mmol) over 5 min. The reaction was stirred 1 h, then chloro(methoxy)methane (12 g, 144 mmol) was added and the reaction stirred an additional 1 h at 0° C. Saturated sodium bicarbonate (500 mL) was added slowly and the suspension stirred 30 min and warmed to rt. The solution was extracted with EtOAc (3×400 mL), the combined organic layers washed with H2O (500 mL), saturated NaCl (500 mL), dried (Na2SO4), and concentrated in vacuo to give the title compound as a brown oil.

Fuente