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. The 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 to give corresponding phthalimide.

Provenance & Evidence