Triphenylphosphine → 1-[2-[(5-Bromo-3-pyridinyl)oxy]ethyl]-2-pyrrolidinone

Participants

Reaction Steps

To a solution of triphenylphosphine (3 g, 12 mmol) in THF (20 mL) at 0° C. was added the following reagents in order in 10 minutes interval: diethyl azodicarboxylate (2 ml, 12 mmol), 1-(2-hydroxyethyl)pyrrolidin-2-one (0.9 ml, 8 mmol), and 5-bromopyridin-3-ol (2 g, 12 mmol). After 20 min, ice bath was removed; the reaction mixture was warmed up to rt and stirred for 20 h. The reaction was stopped, and solvent was removed The crude product was purified using SiO2 chromatography with hexanes:acetone (70%:30%) solvent system to afford the product as white solid. Wt: 900 mg. MS (ESI pos. ion) m/z: 286.3. Calc'd exact mass for C11H13BrN2O2: 285.14. 1H NMR (300 MHz, chloroform-d) δ ppm 2.04 (none, 1H) 2.41 (d, J=16.37 Hz, 2H) 3.51-3.62 (m, 2H) 3.71 (t, J=5.19 Hz, 2H) 4.16 (t, J=5.19 Hz, 2H) 7.37 (d, J=1.90 Hz, 1H) 8.23 (s, 1H) 8.31 (s, 1H).

Provenance & Evidence