Water → 8-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

Participants

Reaction Steps

A 60% strength dispersion of sodium hydride in mineral oil (1.78 g, 44.59 mmol) was taken up in dimethylsulfoxide (25 ml), and trimethylsulfoxonium iodide (9.80 g, 44.6 mmol) was added. The mixture was stirred at room temperature for 45 min. A solution of 1,4-dioxaspiro[4,5]decane-8-carbaldehyde (7.59 g, 44.6 mmol) in dimethylsulfoxide (20 ml) was then added to the mixture. The reaction mixture was stirred at 60° C. for 18 h. After cooling, the mixture was poured into water (100 ml) and extracted with diethyl ether (4×20 ml). The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The crude product (4.64 g) was purified by flash chromatography with cyclohexane/ethyl acetate (4:1).

Provenance & Evidence