Acetone → HCID 54180510, compound

Participants

Reaction Conditions

Reaction Steps

3 g of 2,3,5-tri-O-(p-nitrobenzoyl)-β-D-ribofuranosyl bromide prepared by the procedure described in Example 2 were dissolved in a mixture of 25 ml of acetone and 25 ml of dichloromethane. This solution was cooled to 5° C. and treated with a suspension of silver carbonate (1.25 g) in water (5 ml) with vigorous stirring. Stirring was continued for 90 minutes while the mixture was maintained at 5° C. The mixture was filtered and the filtrate evaporated under reduced pressure to yield a syrup. This syrup was redissolved in 50 ml of dichloromethane, dried over anhydrous MgSO4 and evaporated to yield a syrup which solidified on slow coevaporation with benzene. This yielded 1.76 g (65% yield) of 2,3,5-tri-O-(p-nitrobenzoyl)-D-ribofuranose. Recrystallization of this product from nitromethane yielded colorless needles which had a melting point of 177° to 178° C.

Provenance & Evidence