Phthalimide → HCID 359215, compound

Participants

Reaction Conditions

Reaction Steps

But-2-yne-1,4-diol (8.78 g, 102 mmol), phthalimide (5.00 g, 33.98 mmol) and triphenylphosphine (8.91 g, 33.98 mmol) were combined and dissolved in tetrahydrofuran (165 mL) and then chilled to 0° C. While stirring, diisopropyl azodicarboxylate (10 mL, 50.97 mmol) was added dropwise. The ice bath was removed and the reaction continued to stir at 25° C. for 16 h. The reaction was concentrated in vacuo to give a thick golden oil. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 2-(4-hydroxy-but-2-ynyl)-isoindole-1,3-dione (2.83 g, 39%) as a white powder: ESI-LRMS m/e calcd for C12H9NO3 [M+] 215.1, found 216.3 [M+H+], 431.6 [2M+H+].

Provenance & Evidence