Imidazole → tert-butyl(((5R,6S,6aS)-6-iodo-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)diphenylsilane

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Reaction Steps

To a mixture of (5R,6R,6aR)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-6-ol (from step 5) (32.4 g, 0.0736 mol), triphenylphosphine (57.9 g, 0.2209 mol), Imidazole (15.03 g, 0.2209 mol) in 400 mL anhydrous toluene was added iodine (42.96 g, 0.169 mol) in portions over a period of 30 min and refluxed for 12 h. The mixture was diluted with 300 mL toluene and washed with saturated NaHCO3 solution and saturated sodium thiosulfate solution. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Purification was done by column chromatography using a gradient mixture of hexane and ethyl ether to give 32.08 g (80% yield) of the title compound.

Provenance & Evidence