Reacción #2025291

Ecuación de reacción

sodium hydride

hexyl p-toluenesulfonate

dimethylformamide

(+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine

→

(+)-2-{4-(1-hexyloxyethyl)phenyl}-5-decyloxypyrimidine

Rendimiento 82.1%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto subject to reaction at the same temperature for 2 hours
2. 2
   OtroAfter completion of the reaction
3. 3
   Extracciónextracted with 200 ml of toluene
4. 4
   Otrofollowed by separation
5. 5
   Lavadothe organic phase was washed with water sufficiently
6. 6
   Secadoby drying over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONAfter the solvent was distilled off under reduced pressure
8. 8
   Otrothe resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate)

Procedimiento

Into 20 ml of anhydrous dimethylformamide were dissolved 1.78 g (5 millimole) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)] 70, and then 0.24 g (6 millimole) of 60% sodium hydride was added thereto, followed by stirring at 40° C. for 1 hour. Subsequently, 1.79 g (7 millimole) of hexyl p-toluenesulfonate were added thereto, to subject to reaction at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into 200 ml of water, extracted with 200 ml of toluene, followed by separation thereof, and the organic phase was washed with water sufficiently, followed by drying over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate) to obtain 1.81 g (yield: 82%) of (+)-2-{4-(1-hexyloxyethyl)phenyl}-5-decyloxypyrimidine.

Fuente