반응 #1647

반응 방정식

ethyl acetate

1-[(benzoyloxy)methoxymethyl]thymine

diethyl phosphonomethanol

trimethylsilyl trifluoromethanesulfonate

→

title compound

1-[(Diethylphosphonomethoxy)methoxymethyl]thymine

용매

benzene

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   세척washed with aqueous bicarbonate, brine
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The resultant yellow oil was purified by silica gel column chromatography

실험 절차

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%).

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