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

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Reaction Steps

t-Butyl chloroacetate (13.0 g, prepared according to Org. Synth., Coll. Vol. 4, 263) was added dropwise to a stirred mixture of N-hydroxyphthalimide (14.2 g), triethylamine (23.0 g), and dimethylformamide (30 ml), and the resulting mixture was stirred for 4 hr. The mixture was poured into water (500 ml), and the precipitated solid was collected, washed with water, and dried. Recrystallisation from ethanol gave N-t-butoxycarbonylmethoxyphthalimide (17.26 g, 72%); m.p. 145.6°; τ values (DMSO-d6) 2.09 (4 Ar-H), 5.28 (CH2), 8.56 (But).

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