Acetic Acid → HCID 10995419, compound

Participants

Reaction Steps

To a stirred solution of 3′-O-(4,4′dimethoxytrityl)-5′-formylthymidine (16.3 g, 30.07 mmol) in dioxane (120 ml) at 0° C. was added dropwise, in turn, 36% formaldehyde (24 ml) and 2N NaOH (60 ml). The resulting solution was stirred at room temperature for 6 h. The reaction mixture was cooled to 0° C. and 10% acetic acid in water added dropwise until pH reached 7.5. The mixture was diluted with ethyl acetate (1 L), washed with 10% brine (500 ml, then 2×300 ml), dried (Na2SO4), and concentrated. The crude was purified by chromatography on silica (EtOAc-hexane, 3:1) to give 11.45 g (66.3%) of 3′-O-(4,4′-dimethoxytrityl)-4′-C-hydroxymethylthymidine as a colorless powder.

Provenance & Evidence