Water → HCID 89525592, compound

Participants

Reaction Conditions

Reaction Steps

5.80 g (21 mmol, 1.1 eq) of diphenylphosphoryl azide were added dropwise to a solution of 3.83 g (19 mmol, 1 eq) of (3-fluoromethyloxetan-3-yl)-(5-methylfuran-2-yl)methanol in 50 ml of toluene. The reaction medium was cooled to 0° C. and then 3.15 ml (21 mmol, 1.1 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added dropwise. The reaction medium was stirred at ambient temperature for 15 hours. The (heterogeneous) reaction medium was treated with water and with ethyl acetate and then separated by settling out. The organic phase was washed with 1 N hydrochloric acid, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (column puriFlash IR-50SI/200G, Spot II) eluted with heptane/ethyl acetate (91/9). 2.25 g of 2-[azido-(3-fluoromethyloxetan-3-yl)methyl]-5-methylfuran were obtained in the form of a yellow oil. Yield=53%. TLC SiO2/Heptane:EtOAc (80/20), developing with KMnO4.

Provenance & Evidence