反応 #1647

反応方程式

ethyl acetate

1-[(benzoyloxy)methoxymethyl]thymine

diethyl phosphonomethanol

trimethylsilyl trifluoromethanesulfonate

→

title compound

1-[(Diethylphosphonomethoxy)methoxymethyl]thymine

溶媒

benzene

反応条件

後処理

1. 1
   温度After cooling to room temperature
2. 2
   洗浄washed with aqueous bicarbonate, brine
3. 3
   乾燥dried (MgSO4)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The resultant yellow oil was purified by silica gel column chromatography

実験手順

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%).

出典