Imidazole → HCID 15042006, compound

Participants

Reaction Steps

To a solution of 1.0 g (3.84 mmol) of tert-butyl [(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate, 2.01 g (7.68 mmol) of triphenylphosphine, 0.523 g (7.68 mmol) of imidazole and 11.5 ml of anhydrous benzene was added 1.46 g (5.8 mmol) of iodine with stirring and cooling with ice, and then reacted for 2.5 hours at room temperature. The deposited crystal was filtered, and the obtained crystal was washed with ether. The filtrate and the washings were combined and distilled away under reduced pressure. The residue was purified by subjecting to silica gel column chromatography [eluent: hexane-methylene chloride (1:1), successively ethyl acetate-methylene chloride (1:9)]to give 1.41 g of tert-butyl [(4R,6S)-6-(iodomethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate as syrups (yield: 99%).

Provenance & Evidence