Phenol → 1-Benzhydryl-3-phenoxyazetidine

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Phenol (2.2 g, 23.4 mmol) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 937 mg, 23.4 mmol) in toluene (40 ml) and the mixture was heated at 60° C. for 2 hours. The temperature was then increased to 80° C. and a solution of 1-benzhydrylazetidin-3-yl methanesulfonate (D19) (4.78 g, 14.6 mmol) in toluene (80 ml) was added dropwise. After stirred at 80° C. for 2 hours, the resulting mixture was cooled to room temperature, then washed with water (100 ml) and brine (100 ml), dried over Na2SO4, filtered and evaporated in vacuo. The crude residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate from 30:1 to 20:1. Collected fractions after solvent evaporation were further purified by preparative HPLC to afford the title compound (D20) (1.84 g) as a white solid.

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