Reacción #1144434

Ecuación de reacción

sodium bicarbonate

chloromethyl ethyl ether

5-ethyluracil

bistrimethylsilylacetamide

→

1-ethoxymethyl-5-ethyluracil

Rendimiento 81.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaunder reflux for 15 hours
3. 3
   Filtraciónfiltered through Celite
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Otrodried on magnesium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residue was crystallized from ethyl acetate

Procedimiento

To 100 ml of methylene chloride, 5.1 g (40 mmol) of 5-ethyluracil and 22 ml (88 mmol) of bistrimethylsilylacetamide were added under a nitrogen atmosphere and stirred for 40 minutes at room temperature. To this mixture, 4.1 ml (88 mmole) of chloromethyl ethyl ether and 0.15 g (0.4 mmol) of tetrabutylammonium iodide were added and heated under reflux for 15 hours. Then, the reaction mixture was poured into 50 ml of saturated sodium bicarbonate solution carefully and filtered through Celite. The organic layer was washed with water, dried on magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to obtain 6.4 g of 1-ethoxymethyl-5-ethyluracil (Yield: 81%).

Fuente