4-Nitrophenol → 1-(2-(4-Nitrophenoxy)ethyl)pyrrolidine

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A solution of 10 g of p-nitrophenol (72 mmol) in 100 mL dry THF was treated with 28.28 g (108 mmol) of triphenyl phosphine. The solution was cooled to 0° C. then treated with 18.78 g (108 mmol) diethyl azodicarboxylate. After stirring for 30 min at 0° C., 12.4 g (108 mmol) 1-(2-hydroxyethyl)pyrrolidine was added. The cooling bath was removed and the reaction allowed to stir overnight at ambient temperature. EtOAc was added (300 mL) and the mixture was extracted twice with 200 mL 1 N H2SO4. The combined extracts were washed twice with 200 mL EtOAc, made basic with 5 N NaOH and extracted three times with 150 mL EtOAc. The extracts were dried over MgSO4 and concentrated under vacuum to an oil which was purified by chromatography (SiO2 ; 1% MeOH in CHCl3) to recover 7.56 g (32 mmol, 44%) of the desired compound as a solid.

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