N ‐Vinylphthalimide

image [3485‐84‐5] C 10 H 7 NO 2 (MW 173.05) InChI = 1S/C10H7NO2/c1‐2‐11‐9(12)7‐5‐3‐4‐6‐8(7)10(11)13/h2‐6H,1H2 InChIKey = IGDLZDCWMRPMGL‐UHFFFAOYSA‐N (reagent in cyclopropanation reaction, cycloaddition reactions, metal‐catalyzed reactions, and radical addition reactions) Alternative Name(s): 2‐vinylisoindoline‐1,3‐dione. Physical Data: mp 74–75 °C. 1 ; d 1.321 g cm −3 . 2 Form Supplied in: solid; commercially available. Preparation: the title reagent is prepared by dissolving phthalimide (0.594 g) in vinyl acetate (10 mL) and adding catalytic amounts of Na 2 PdCl 4 (11.2 mg) under argon. The mixture is then heated under reflux for 8 h. Activated charcoal (15 mg) is then added and after stirring for 10 min, diethyl ether (20 mL) is added. The solids are removed by filtration and the filtrate is concentrated under reduced pressure. The crude product is extracted with diethyl ether and the extracts are dried over MgSO 4 and concentrated under reduced pressure. The residue is purified by crystallization. 3 Purification: recrystallization from petroleum benzine to form colorless needles. 4 Handling, Storage, and Precautions: should be stored in a closed container and placed in a dry, cool, and well‐ventilated storage. This reagent is incompatible with strong oxidizing agents.