Sodium Iodide → 1-(Tert-butyldimethylsilyl)oxy-3-iodocyclohexane

Participants

Reaction Steps

A solution of 3-(tert-butyldimethylsilyl)oxy-1-(methylsulfonyloxy)cyclohexane (15.9 g) and sodium iodide (8.5 g) in N,N-dimethylformamide (80 ml) was heated at 100° C. for 3 hours with stirring. After cooled to ambient temperature, a reaction mixture was poured into a mixture of ethyl acetate (250 ml) and n-hexane (150 ml), and insoluble material was removed by filtration. Mother liquor was washed in turn with water (100 ml×3), 5% sodium thiosulfate in water (50 ml), and saturated sodium chloride in water (100 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (300 ml) eluting with 10% ethyl acetate in n-hexane to give 3-(tert-butyldimethylsilyl)oxy-1-iodocyclohexane (cis and trans mixture).

Provenance & Evidence