1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 1-(4-((3-(azido(phenyl)methyl)phenoxy)methyl)-phenyl)cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 1-(4-((3-(hydroxy(phenyl)methyl)phenoxy)-methyl)phenyl)cyclopropanecarboxylate (1.824 g, 4.695 mmol) in toluene (21.8 mL) under an atmosphere of nitrogen, was added diphenylphosphoryl azide (1.21 mL, 5.635 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (0.84 mL, 5.635 mmol). The reaction mixture was stirred at 100° C. for 3 hours and then allowed to cool to room temperature. The reaction was quenched by addition of saturated aqueous ammonium chloride solution and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine and dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford a brown oil. The crude material was purified by silica gel chromatography eluting with 0-14% ethyl acetate in iso-hexane to afford the title compound as a colourless oil (1.214 g, 62%).

Provenance & Evidence