반응 #1144432

반응 방정식

acetic acid

lithium diisopropylamide

1-ethoxymethyl-5-ethyluracil

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

diphenyl disulfide

tetrahydrofuran

→

1-ethoxymethyl-5-ethyl-6-phenylthiouracil

수율 32.0%

용매

ethyl acetate

반응 조건

후처리

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

실험 절차

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%).

출처