Dimethylformamide → 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

A mixture of bromocyclopentane (14.9 g), N-hydroxyphthalimide (16.3 g), triethylamine (15 ml), and dimethylformamide (30 ml) was stirred for 16 hours, then poured into water (500 ml). The oily mixture was extracted with ethyl acetate, and the combined extracts, after washing (water), drying, and removal of solvent gave a while solid. This solid was recrystallised from ethanol to give N-cyclopentyloxyphthalimide (11.37 g, 49%); m.p. 81.2°-82.5°; λmax. (CHBr3) include 1780, 1720 cm-1 (CO--N--CO), 970 cm-1 ##STR72## τ values (DMSO-d6) 2.08 (4 Ar-H), 5.12 (cyclopentyl 1-H), 8.18 (4-CH2).

Provenance & Evidence