Triphenylphosphine → 2-(2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpyrrolidine

Participants

Reaction Steps

11.3 g of diethyl azodicarboxylate were added dropwise, whilst ice-cooling and stirring, to a solution of 10.6 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 20), 8.4 g of 1-methyl-2-pyrrolidylethanol and 17 g of triphenylphosphine in 200 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 15 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 5.70 g (yield 36%) of the title compound as a colorless oil.

Provenance & Evidence