N-Hydroxyphthalimide → Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

Participants

Reaction Steps

In N,N-dimethylformamide (200 ml) ar dissolved 24.5 g (0.15 mole) of N-hydroxyphthalimide and 29.3 g (0.15 mole) of tert-butyl bromoacetate, and 20.7 g (0.15 mole) of powdered potassium carbonate is added to the solution under ice-cooling with stirring. The reaction solution is stirred under ice-cooling for 30 minutes and then at room temperature for 20 hours, and poured into 2 l of ice cold water. The crystals that separate out are recovered by filtration, washed with 1 l of water and 500 ml of hexane successively and dried under reduced pressure at 40° C. to give 39.7 g (95.5%) of N-(tert-butoxycarbonylmethoxy)phthalimide as colorless crystals. This product is to be used in the subsequent reaction, and part of this product, when recrystallized from etyyl acetate-n-hexane (1:2), exhibits a melting point of 145°-146° C.

Provenance & Evidence