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

Participants

Reaction Steps

Triphenyl phosphine (5.94 g, 22.65 mmol) and imidazole (22.65 mmol) were dissolved in a mixed solution (120 ml) of diethyl ether-acetonitrile (3:1). Iodine (5.75 g, 22.65 mmol) was added thereto under cooling on ice and the mixture was stirred at room temperature for 30 minutes. The solution was cooled on ice again, (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (3.0 mmol, 20.59 mmol) was added thereto and the mixture was stirred at room temperature for 24 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 residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 3.20 g (61%) of the title compound in the form of a yellowish oily product.

Provenance & Evidence