1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89525566, compound

Participants

Reaction Conditions

Reaction Steps

5.30 g (19 mmol, 1.1 eq) of diphenylphosphoryl azide were added dropwise to a solution of 3.02 g (17 mmol, 1 eq) of (5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methanol in 50 ml of toluene. The reaction medium was cooled to 0° C. and then 2.9 ml (19 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 23 hours. The reaction medium was separated by settling out and the organic phase was washed with water and then with 1 N hydrochloric acid, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (column Analogix SF40-150 g, Spot II) eluted with heptane/ethyl acetate (95/5). 1.68 g of 2-[azido-(3-methyloxetan-3-yl)methyl]-5-methylfuran were obtained in the form of an orange oil. Yield=48%.

Provenance & Evidence