Water → HCID 89525595, compound

Participants

Reaction Conditions

Reaction Steps

39.3 ml (0.18 mol; 1.2 eq) of diphenylphosphoryl azide and then 27.3 ml (0.18 mol; 1.2 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added dropwise to a solution of 30.21 g (0.15 mol; 1.0 eq) of (5-methylfuran-2-yl)-(tetrahydrothiophen-2-yl)methanol in 350 ml of toluene cooled to 0° C. The mixture was allowed to return to ambient temperature gently and was then stirred for 2 days. The reaction medium was treated with water and extracted with ethyl acetate. The organic phases were combined, washed with a 1 M sodium hydrogen phosphate solution, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (column puriFlash IR-50SI/800G, puriFlash) eluted with heptane/ethyl acetate (95/5). 26.95 g of 2-[azido-(tetrahydrothiophen-2-yl)methyl]-5-methylfuran were obtained (mixture of the 2 diastereoisomers). Yield=79%.

Provenance & Evidence