N-Hydroxyphthalimide → HCID 23353087, compound

Participants

Reaction Steps

33.4 g (0.205 mol) of N-hydroxyphthalimide and 53.8 g (0.205 mol) of triphenylphosphine were added to a solution of 33.1 g (0.186 mol) of 5-hydroxy-1-(4-fluorophenyl)-1-pentyne in 430 ml of dry tetrahydrofuran. 35.7 g (0.205 mol) of diethyl azodicarboxylate were then added dropwise inthe course of 2.5 hours under temperature control (not more than 40°C.). Stirring was carried out overnight at room temperature, the mixture was evaporated down under reduced pressure and the residue was taken up with 300 ml of dichloromethane. The solution was washed twice with sodium carbonate solution and once with saturated sodium chloride solution. Afterthe solution had been dried and evaporated down, the crude product was purified by chromatography over silica gel. The eluent used was initially dichloromethane/n-hexane and then pure dichloromethane. Yield: 82%; mp.: 85°-88° C.

Provenance & Evidence