3-(Phenylmethoxy)benzenemethanol → 1-(Azidomethyl)-3-(phenylmethoxy)benzene

Participants

Reaction Steps

To a stirred solution of 3-benzyloxybenzyl alcohol (5.0 g, 23.3 mmol) and diphenylphosphoryl azide (7.7 g, 28.0 mmol) in dry toluene (40 mL) at 0° C., was added 1,8-diazabicyclo[5.4.0]undec-7-ene (3.9 g, 25.6 mmol). The resulting mixture was allowed to warm to ambient temperature, and stirred under argon for 18 hours, then washed with water (2×15 mL), then 5% hydrochloric acid (15 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane—4% EtOAc to yield the product as a colorless oil.

Provenance & Evidence