Sodium Hydroxide → HCID 21862857, compound

Participants

Reaction Steps

0.15 g (4.0 mmol) of lithium aluminum hydride was suspended in 25 ml of diethyl ether, and a solution of 0.98 g (2.6 mmol) of 1-(4-fluorophenyl)-4-methoxycarbonyl-2-(4-methylsulfonylphenyl)pyrrole [prepared as described in step (iii) above] in 20 ml of methylene chloride was added dropwise to the suspension whilst it was heated under reflux in a nitrogen atmosphere. The mixture was stirred under reflux for 1 hour, and then 0.15 ml of water, 0.15 ml of a 15% w/v aqueous solution of sodium hydroxide and 0.45 ml of water were added to the mixture, in that order. The mixture was then stirred at room temperature for 30 minutes. At the end of this time, the mixture was dehydrated by adding anhydrous magnesium sulfate, and it was filtered over a Celite (trade mark) filter aid. The solvent was then removed from the filtrate by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 2:1 by volume mixture of ethyl acetate and hexane, to give 0.69 g (yield 76%) of the title compound as a white powder, melting at 88-90° C.

Provenance & Evidence