Dimethylformamide → HCID 54105048, compound

Participants

Reaction Steps

0.38 ml (0.00408 mole) of phosphorus oxychloride was added to 0.29 g (0.00397 mole) of dry dimethylformamide and the mixture was stirred at room temperature for 30 minutes. A solution of 0.89g (0.00297 mole) of 1-(2-butenyl)-5-[3-(4-fluorophenyl)propionyl]-2,3-dimethylpyrrole in 4 ml of dichloromethane was added dropwise to the mixture and stirred at room temperature for 30 minutes. The reaction mixture was poured into ice-water and neutralized with an aqueous solution of sodium hydroxide. The aqueous mixture was extracted with 50 ml each of dichloromethane for three times. The extract was washed with 30 ml of a saturated aqueous solution of sodium hydrogencarbonate and 30 ml of a saturated aqueous solution of sodium chloride in turn and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography through silica gel using a 1:12 to 1:9 mixture of ethyl acetate and hexane as an eluent to give 0.41 g of the title compound (cis/trans=22/78) as a yellow oil.

Provenance & Evidence