Reaction #1144434

Reaction equation

sodium bicarbonate

chloromethyl ethyl ether

5-ethyluracil

bistrimethylsilylacetamide

→

1-ethoxymethyl-5-ethyluracil

Yield 81.0%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureunder reflux for 15 hours
3. 3
   Filtrationfiltered through Celite
4. 4
   WashThe organic layer was washed with water
5. 5
   Otherdried on magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was crystallized from ethyl acetate

Procedure

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%).

Source