Réaction #1647

Équation de réaction

ethyl acetate

1-[(benzoyloxy)methoxymethyl]thymine

diethyl phosphonomethanol

trimethylsilyl trifluoromethanesulfonate

→

title compound

1-[(Diethylphosphonomethoxy)methoxymethyl]thymine

Solvants

benzene

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to room temperature
2. 2
   Lavagewashed with aqueous bicarbonate, brine
3. 3
   Séchagedried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe resultant yellow oil was purified by silica gel column chromatography

Mode opératoire

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%).

Source