Reacción #165103

Ecuación de reacción

(4-chloro-pyridine-2-yl)-methanol

thionyl chloride

sodium hydrogencarbonate

→

title compound

Rendimiento 59.9%

4-Chloro-2-chloromethyl-pyridine

Rendimiento 59.9%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónwas then extracted with ethyl acetate
2. 2
   OtroThe organic layer was separated
3. 3
   Lavadowashed with water and saturated aqueous sodium chloride
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   ConcentraciónThe filtrate was concentrated under a reduced pressure
7. 7
   Otrothe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1)

Procedimiento

To a mixture of (4-chloro-pyridine-2-yl)-methanol (146.8 mg, 1.0 mmol) described in Manufacturing Example 51-1-1 and toluene (3 mL) was added thionyl chloride (112 μL, 1.53 mmol) on an ice bath, which was stirred for 1 hour 15 minutes at room temperature. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (97 mg, 59%).

Fuente