Imidazole → (4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane

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Reaction Steps

Triphenyl phosphine (31.0 g, 118.21 mmol) and imidazole (8.05 g, 118.21 mmol) were dissolved in a mixed solution (400 ml) of diethyl ether-acetonitrile (3:1), iodine (30.0 g, 118.21 mmol) was added thereto under cooling on ice and the mixture was stirred at room temperature for 3 hours. The solution was cooled on ice again, a mixed solution (100 ml) of (4S)-(+)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (15 g, 98.51 mmol) in diethyl ether-acetonitrile (3:1) was added thereto and stirred at room temperature for 18 hours. A saturated sodium thiosulfate aqueous solution was added to the reaction solution under cooling on ice and stirred for a while. The solution was extracted with diethyl ether and the extract was washed with saturated sodium chloride solution. The solvent was removed under reduced pressure and the obtained residue was triturated by adding a mixed solvent of ether/hexane to remove the insoluble material by filtration. The filtrate was concentrated under reduce pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 23.1 g (92%) of the title compound in the form of a colorless clear oily product.

Provenance & Evidence