反应详情

温度

60 °C

A 1.66 g quantity of 2,4,6-trimethylbenzyl chloride was added to a solution of 4.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine, 2.30 g of potassium hydroxide and 1.47 g of sodium iodide in 50 ml of dried dioxane. The mixture was stirred at 60° C. for 3 hours. The solvent was distilled off, and ethylacetate and water were added to the residue. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was distilled off and the residue was dissolved in 50 ml of a 80% solution of acetic acid. The resulting solution was left to stand at 70° C. for 2 hours. The reaction mixture was concentrated and water was added to the concentrate. The mixture was rendered weakly basic with an aqueous solution of sodium hydroxide and washed with ether. The aqueous layer was made weakly acidic with a 6N solution of hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate and concentrated. Ether was added to the concentrate to deposit solids and the solids were recrystallized from ethanol, giving 1.69 g of the title compound in a yield of 55%.

1. distillationThe solvent was distilled off
2. additionethylacetate and water were added to the residue
3. washThe ethyl acetate layer was washed with water
4. dry with materialdried over anhydrous sodium sulfate
5. distillationThe ethyl acetate was distilled off
6. dissolutionthe residue was dissolved in 50 ml of a 80% solution of acetic acid
7. waitThe resulting solution was left
8. waitto stand at 70° C. for 2 hours
9. concentrationThe reaction mixture was concentrated
10. additionwater was added to the concentrate
11. washwashed with ether
12. extractionextracted with ethyl acetate
13. washThe ethyl acetate layer was washed with water
14. dry with materialdried over anhydrous sodium sulfate
15. concentrationconcentrated
16. additionEther was added to the
17. concentrationconcentrate
18. customthe solids were recrystallized from ethanol