N-Hydroxyphthalimide → Ethyl 4-((1,3-dioxoisoindolin-2-yl)oxy)butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-bromo-n-butyrate (1.2 g, 6.13 mmol) in dimethylformamide (9 ml), N-hydroxyphthalimide (1.5 g, 9.19 mmol) and Hunig base (N,N-diisopropylethylamine, 2.13 mL) were added at room temperature, and the mixture was stirred at 80° C. overnight. The reaction solution was poured into saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with ethyl acetate (3×40 ml). The combined organic layer was washed with saturated brine (2×30 ml), dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (100 g, n-hexane/ethyl acetate=2:1) to give 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-butyric acid ethyl ester (1.47 g, 100%).

Provenance & Evidence