Phthalimide → N-(3-Butynyl)phthalimide

Participants

Reaction Conditions

Reaction Steps

Diisopropyl azodicarboxylate (316 g, 1.56 mol) was added to a solution of triphenylphosphine (PPh3) (393 g, 1.50 mol), 3-butyn-1-ol (105 g, 1.50 mol) and phthalimide (200 g, 1.36 mol) in toluene (1600 mL) which was pre-cooled with a −5° C. cooling bath at such a rate that temperature of the reaction mixture was kept between 15-25° C. The addition time was 50 min. The cooling bath was removed after the addition was finished. The reaction mixture was allowed to warm to 15-25° C. and stirred for 1 h. Then methanol (800 mL) was added. The mixture was stirred for 30 min and then filtered. The crude product was washed with methanol and dried to give a white solid (218 g) in 80% yield 99.8% purity by area. 1H NMR (DMSO-d6): δ 7.88 (m, 4 H), 3.72 (t, 2 H, J=7.0 Hz), 2.83 (t, 1 H, J=2.7 Hz), 2.55 (m, 2 H).

Provenance & Evidence