Dichloromethane → HCID 18634663, compound

Participants

Reaction Steps

Pivaloyl chloride (0.3 ml, 2.56 mmoles) was added to a cooled, stirred solution of 2'-deoxy-5-ethynyluridine (0.5 g, 1.98 mmols) in dry pyridine (5 ml) and stirring was maintained at room temperature for 3 hours. TLC in CH2Cl2 /MeOH (19:1) revealed complete reaction. The mixture was poured onto ice/water, methylene chloride added, the organic layer separated and washed with water, dried with sodium sulphate and evaporated to dryness. The residue was chromatographed on silica gel eluted with CH2Cl2 /MeOH. The first product was triturated with hexane to give 2'-deoxy-3',5'-di-O-pivaloyl-5-ethynyluridine. M.p. 151° C.

Provenance & Evidence