Methyl vinyl ketone → 2-(3-Oxobutyl)isoindoline-1,3-dione

Participants

Reaction Steps

To a well-stirred milky suspension of phthalimide (60.0 g, 408.0 mmol, 1.00 eq.) and 3-buten-2-one (33.2 mL, 408.0 mmol, 1.00 eq.) in anhydrous ethyl acetate (400 mL) under N2, a freshly prepared yellow homogeneous solution of sodium ethoxide (1.4 g, 20.4 mmol, 0.05 eq.) in anhydrous ethanol (100 mL) was added dropwise (over 35 min.). After completion of the addition, the resulting slightly yellow heterogeneous mixture was further stirred at r.t. for 2 hours. The beige heterogeneous mixture was then refluxed (oil bath temperature=90° C.) for 2 hours. The resulting orange homogeneous solution was then allowed to slowly cool down to r.t. The resulting heterogeneous mixture was concentrated to dryness in vacuo to afford a beige solid which was recrystallized from EtOH to afford the title compound as a beige solid.

Provenance & Evidence