N-Hydroxyphthalimide → N-[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]phthalimide

Participants

Reaction Steps

4,7-Dichloro-2,2-diphenyl-1,3-benzodioxol-5-methanol (250 mg) (0.67 mmol), 108 mg (0.67 mmol) of N-hydroxyphthalimide and 175 mg (0.67 mmol) of triphenylphosphine are suspended in 20 ml of absolute tetrahydrofuran. 128 mg (0.73 mmol) of diethyl azodicarboxylate are added dropwise at 0° C. while stirring. The mixture is stirred at 0° C. for 1 hour and at room temperature for 24 hours. Subsequently, the solvent is removed in a high vacuum. The residue is crystallized and recrystallized from ethanol/diethyl ether. There are obtained 230 mg of N-[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]phthalimide as white crystals of m.p. 127°-129° C.

Provenance & Evidence