Ethanol → 2'-Deoxy-5'-O-(triphenylmethyl)uridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2'-deoxyuridine (100 g, 0.44 mol) and triphenylmethyl choride (147 g, 0.53 mol) in 250 mL of pyridine was heated at 100° C. for 30 minutes. One-third of the cooled solution was added at a slow flow rate to a mixture of ice water (2:3) in a commercial blender blending for 3-5 minutes after adding the solution. The resulting white precipitate was filtered and washed twice, stirring in 2 L of water. Recrystallization was accomplished by refluxing the product in a benzene-acetone solution (1:1) for 15 minutes, yielding 128 g (62%). The compound softened at 76° C., began to melt at 152-155° C., and darkened in color at 155-159° C. Rf =0.71 (CHCl3 --EtOH, 4:1).

Provenance & Evidence