Reaktion #1647

Reaktionsgleichung

ethyl acetate

1-[(benzoyloxy)methoxymethyl]thymine

diethyl phosphonomethanol

trimethylsilyl trifluoromethanesulfonate

→

title compound

1-[(Diethylphosphonomethoxy)methoxymethyl]thymine

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Waschenwashed with aqueous bicarbonate, brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe resultant yellow oil was purified by silica gel column chromatography

Vorschrift

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%).

Quelle