Phthalimide → HCID 53485842, compound

Participants

Reaction Conditions

Reaction Steps

Into a reaction vessel were put phthalimide (2.00 g, 13.6 mol), (R)-epichlorohydrin (2.52 g, 27.2 mol), anhydrous sodium carbonate (144 mg, 1.36 mol), benzyltrimethylammonium chloride (252 mg, 1.36 mol) and isopropanol (13 ml) and the mixture was reacted at room temperature for 15 hours. After removal unreacted epichlorohydrin, to the residue was added isopropanol (13 ml) and the mixture is cooled to 20° C. Then thereto was gradually dropped a mixture of potassium tert-butoxide (1.83 g, 16.3 mol) and isopropanol (7 ml) and the mixture was stirred for 1 hour at the same temperature. The solvent was removed and to the residue was added ethyl acetate (13 ml). The mixture was washed with water (7 ml), and then ethyl acetate was removed to give crude (R)-glycidylphthalimide (2.16 g, yield 78%, optical purity 98% e.e.) as white crystals.

Provenance & Evidence