Trityl chloride → 2'-Deoxy-5'-O-(triphenylmethyl)uridine

Participants

Reaction Conditions

Reaction Steps

2′-deoxyuridine (4.00 g, 17.5 mmol) and triphenylmethyl chloride (5.37 g, 19.25 mmol) were stirred in anhydrous pyridine (70 ml) at 50° C. overnight. Additional triphenylmethyl chloride (1.00 g, 3.59 mmol) was added after 18 hours, and the mixture was stirred for a further 4 hours at 50° C. The reaction mixture was then poured into ice-H2O (300 ml) and stirred vigorously. The precipitate was extracted with EtOAc (3×100 ml). The organic solution was then washed with 0.5 M HCl (4×100 ml), dried with MgSO4 and filtered. The filtrate was then washed further with EtOAc, which was then evaporated, and finally with DCM. Solvent was removed using a Buchi rotary evaporator, and finally with the vacuum pump.

Provenance & Evidence