Isopropanol → 2-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

To a suspension of N-hydroxyphthalimide (2.52 g, 15.45 mmol) in THF (60 ml) was added triphenylphosphine (4.10 g, 15.63 mmol), 2-propanol (1.2 ml, 15.67 mmol) and diethyl azodicarboxylate (2.68 ml, 17.0 mmol) and the reaction stirred overnight. The mixture was concentrated and purified by column chromatography on silica gel (Hexanes/EtOAc, 4:1) to afford 2-isopropoxy-isoindole-1,3-dione (2.59 g, 82%) as a white solid. 1H NMR (CDCl3) δ 1.38 (d, 6H, J=6 Hz), 4.52-4.58 (m, 1H), 7.73-7.76 (m, 2H), 7.83-7.85 (m, 2H).

Provenance & Evidence