反応 #1144432

反応方程式

acetic acid

lithium diisopropylamide

1-ethoxymethyl-5-ethyluracil

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

diphenyl disulfide

tetrahydrofuran

→

1-ethoxymethyl-5-ethyl-6-phenylthiouracil

収率 32.0%

溶媒

ethyl acetate

反応条件

後処理

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

実験手順

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%).

出典