反应 #1647

反应方程式

ethyl acetate

1-[(benzoyloxy)methoxymethyl]thymine

diethyl phosphonomethanol

trimethylsilyl trifluoromethanesulfonate

→

title compound

1-[(Diethylphosphonomethoxy)methoxymethyl]thymine

溶剂

benzene

反应条件

后处理

1. 1
   温度After cooling to room temperature
2. 2
   洗涤washed with aqueous bicarbonate, brine
3. 3
   干燥dried (MgSO4)
4. 4
   过滤filtered
5. 5
   浓缩concentrated in vacuo
6. 6
   其他The resultant yellow oil was purified by silica gel column chromatography

实验过程

To a solution of 1-[(benzoyloxy)methoxymethyl]thymine (2.9 g, 10 mmol) and diethyl phosphonomethanol (1.85 g, 11 mmol) in benzene (180 mL) was added trimethylsilyl trifluoromethanesulfonate (0.05 mL) via a syringe under nitrogen. The solution was heated at 85° C. for 20 min. After cooling to room temperature, ethyl acetate (50 mL) was added and washed with aqueous bicarbonate, brine dried (MgSO4), filtered and concentrated in vacuo. The resultant yellow oil was purified by silica gel column chromatography using CH2Cl2 /5% MeOH as an eluent to give the title compound as a white oil: yield 980 mg (30%).

来源