Tetrahydrofuran → Tributyl(iodomethyl)stannane

Participants

Reaction Conditions

Reaction Steps

To a mixture of triphenylphosphine (70 g, 0.27 mol) and tetrahydrofuran (500 ml) was added dropwise a mixture of N-iodosuccinimide (60 g, 0.27 mmol) and tetrahydrofuran (500 ml) at 0° C. (external temperature). Then, the reaction mixture was stirred at 0° C. (external temperature) for 30 minutes. To the mixture was added dropwise tributylstannyl-methanol (71 g, 0.22 mol) at 0° C. (external temperature). Then, the reaction mixture was stirred at 0° C. (external temperature) for 20 minutes. The reaction mixture was stirred at room temperature overnight. To the reaction mixture were added diethyl ether and water, and the organic layer was separated. The organic layer was sequentially washed with an aqueous saturated sodium thiosulfate solution and an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. To the residue was added heptane (400 ml), followed by filtration. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (heptane) to obtain the title compound (90 g, 0.21 mol, 94%).

Provenance & Evidence