Реакция #1144434

Уравнение реакции

sodium bicarbonate

chloromethyl ethyl ether

5-ethyluracil

bistrimethylsilylacetamide

→

1-ethoxymethyl-5-ethyluracil

Выход 81.0%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Температураheated
2. 2
   Температураunder reflux for 15 hours
3. 3
   Фильтрацияfiltered through Celite
4. 4
   ПромывкаThe organic layer was washed with water
5. 5
   Другоеdried on magnesium sulfate
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe residue was crystallized from ethyl acetate

Методика

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%).

Источник