Dichloroacetic Acid → HCID 70399831, compound

Participants

Reaction Steps

A solution of 2.759 g of 3'-O-acetyl-2'-deoxy-5-ethyluridine, 5.75 g of dicyclohexylcarbodiimide and 0.375 ml of dichloroacetic acid in 24 ml of dimethyl sulphoxide was stirred at room temperature for 27 hours. 0.375 ml of pyridine and 4.286 g of [3-(2,6-dichlorophenyl)-2-oxopropylidene]triphenylphosphorane were added and the mixture was stirred for a further 23 hours. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in 100 ml of ethyl acetate and the solution was washed twice with 100 ml of water each time, dried over anhydrous sodium sulphate and evaporated. The resulting gum was subjected to flash chromatography on a column of silica gel using ethyl acetate/hexane (2:1) for the elution. There were obtained 3.84 g of (E)-3'-O-acetyl-5'-[3-(2,6-dichlorophenyl)-2-oxopropylidene]-2',5'-dideoxy-5-ethyluridine in form of a white solid of melting point 165° C.

Provenance & Evidence