Epichlorohydrin → HCID 5328503, compound

Participants

Reaction Steps

A solution of 5-hydroxy-1-phenylbenzimidazole (Example 14) (0.24 g, 1.14 mmol) 1:1 THF/DMF (5 mL) was added under nitrogen to a stirred suspension of sodium hydride (41 mg of a 60% dispersion in oil, 1.71 mmol). After 5 minutes, epichlorohydrin (98 μL, 1.26 mmol) was added, and the solution was refluxed for 4 hours. The cooled solution was partitioned between diethyl ether and water, and the extract was washed with 2N NaOH and worked up to give an oil which was chromatographed on silica gel. EtOAc/petroleum ether (1: 1) eluted foreruns, while EtOAc eluted the epoxide Example 34 (0.14 g, 46%): mp (EtOAc/petroleum ether) 96-97.5° C.

Provenance & Evidence