Water → Phthalimide

Participants

Reaction Steps

The title B tosylate (19.2 mmol) and purified potassium phthalimide (6.4 g, 34.6 mmol, 1.8 equiv.) in dimethylsulfoxide (70 ml, Burdick & Jackson) are heated at 90°-100° C. for 21/2 hours (checked by TLC Et2O-pet ether 2:1, no tosylate remaining). After cooling to room temperature, water (90 ml) is added. The mixture is poured into ice water (~350 ml) and stirred 30 minutes. A solid is harvested by filtration and washed with more water. The solid is dissolved in warm ethyl acetate (150 ml), washed with water (3×50 ml), dried (MgSO4), filtered and freed of solvent in vacuo. The remaining solid is recrystallized from isopropyl ether (~150 ml) to give corresponding phthalimide.

Provenance & Evidence