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

Participants

Reaction Steps

A mixture of cesium trichloride (24.9 g) in tetrahydrofuran (45 ml) was stirred at room temperature for 5 hours. 1,4-Dioxa-spiro[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 phenylmagnesium chloride (3.0M solution in dimethyl ether) (33.7 ml) at 0° C. The reaction mixture was quenched with 10% acetic acid aqueous solution. Dimethyl ether was added to the solution. The organic layer was washed with brine, sodium hydrogen carbonate solution and 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 (3:1 hexane-ethyl acetate elution) to give 8-phenyl-1,4-dioxaspiro[4.5]decan-8-ol (5.94 g).

Provenance & Evidence