反应 #1144432

反应方程式

acetic acid

lithium diisopropylamide

1-ethoxymethyl-5-ethyluracil

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

diphenyl disulfide

tetrahydrofuran

→

1-ethoxymethyl-5-ethyl-6-phenylthiouracil

收率 32.0%

溶剂

ethyl acetate

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise over 15 minute
2. 2
   其他to react for 30 minutes
3. 3
   其他brought to room temperature
4. 4
   洗涤The mixture was washed with water (3 mix 5) and saturated aqueous solution of sodium hydrogencarbonate (twice),
5. 5
   其他dried on magnesium sulfate
6. 6
   浓缩′ concentrated under reduced pressure
7. 7
   其他The residue was purified by silica gel chromatography (ethyl acetate/hexane=3:17)
8. 8
   其他crystallized from ethyl acetate

实验过程

Then, 2.2 ml of lithium diisopropylamide (4.4 mmol) solution in tetrahydrofuran (2.1M) was added to 6 ml of tetrahydrofuran under a nitrogen atmosphere at −70° C., to which a solution of 0.40 g (2.0 mmol) of 1-ethoxymethyl-5-ethyluracil in 3 ml of tetrahydrofuran was added dropwise over 15 minute. After stirring for 1 hour at −70° C., the reaction mixture was added with a solution of 0.57 g of diphenyl disulfide in 2 ml of tetrahydrofuran dropwise over 10 minutes and allowed to react for 30 minutes. The reaction mixture was added with 1 ml of acetic acid, brought to room temperature and then added with 30 ml of ethyl acetate. The mixture was washed with water (3 mix 5) and saturated aqueous solution of sodium hydrogencarbonate (twice), dried on magnesium sulfate and′ concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexane=3:17) and crystallized from ethyl acetate to obtain 0.61 g of 1-ethoxymethyl-5-ethyl-6-phenylthiouracil (Yield: 32%).

来源