1,4-Dioxaspiro[4.5]decan-8-one → 8-Cyclohexyl-1,4-dioxaspiro[4.5]decan-8-ol

Participants

Reaction Steps

A mixture of cesium trichloride (5.0 g) in tetrahydrofuran (45 ml) was stirred at room temperature for 6 hours. 1,4-Dioxaspiro[4.5]decan-8-one (1.4 g) was added to the solution and stirred at room temperature for 1 hour. To the solution was added dropwise with stirring cyclohexylmagnesium chloride (2.0M solution in diethyl ether) (6.7 ml) at 0° C. The reaction mixture was quenched with 10% acetic acid aqueous solution. Diethyl ether was added to the solution. The organic layer was taken, washed with brine, sodium hydrogen carbonate solution, brine and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 8-cyclohexyl-1,4-dioxaspiro[4.5]decan-8-ol (1.266 g).

Provenance & Evidence