Phthalimide → HCID 11608126, compound

Participants

Reaction Conditions

Reaction Steps

Into a reaction vessel were put phthalimide (200.0 g, 1.36 mol), (S)-epichlorohydrin (226.4 g, 2.45 mol), anhydrous sodium carbonate (14.40 g, 0.136 mol), benzyltrimethylammonium chloride (25.24 g, 0.136 mol) and isopropanol (1.2 L) and the mixture was reacted at 25° C. for 22 hours to give crude N-(3-chloro-2-hydroxypropyl)phthalimide. The reaction mixture is cooled to 15° C. and then thereto was dropped a mixture of potassium tert-butoxide (183.0 g, 1.63 mol) and isopropanol (0.8 L) over a two hours period and the mixture was stirred for 2 hours at the same temperature. The solvent was removed and to the residue was added ethyl acetate (1.3 L). The mixture was washed with water (0.65 L), and then ethyl acetate was removed to give crude (S)-glycidylphthalimide. The crude product was crystallized from ethyl acetate-hexane to give the object (S)-glycidylphthalimide (206.3 g, yield: 75%, optical purity: 98% e.e.) as white crystals. mp 99–101° C.

Provenance & Evidence