Dimethylformamide → 4-Azido-2-fluorocyclohexyl 2-phenylethyl ether

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Reaction Conditions

Reaction Steps

Sodium azide (0.500 g, 7.69 mmol) was added to a N,N-dimethylformamide (10 mL) solution of 3-Fluoro-4-(2-phenylethoxy)cyclohexyl methanesulfonate (0.597 g, 1.89 mmol) under nitrogen. The resulting mixture was heated at 50° C. for 24 h, then cooled and poured into saturated sodium bicarbonate. The aqueous mixture was extracted with ethyl acetate (3×) and the combined organic extracts were washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Flash column chromatography (hexane:ethyl acetate, e 90:10) gave 4-Azido-2-fluorocyclohexyl 2-phenylethyl ether as a colorless oil (0.355 g, 71% yield).

Provenance & Evidence