Tributylstannane → Stannane, tributyl(methoxymethyl)-

Participants

Reaction Steps

To a mixture of diisopropylamine (9.4 ml, 67 mmol) and tetrahydrofuran (150 ml) was added dropwise n-butyllithium (2.4M n-hexane solution, 25 ml, 61 mmol) at −78° C. (external temperature) Then, the reaction mixture was stirred for 30 minutes. To the mixture was added dropwise tributyltin hydride (16 ml, 61 mmol) at −78° C. (external temperature). Then, the reaction mixture was stirred at 0° C. (external temperature) for 30 minutes. After the reaction mixture was cooled at −78° C. (external temperature), chloromethyl methyl ether (4.6 ml, 61 mmol) was added dropwise to the reaction mixture. After the mixture was stirred at room temperature (external temperature) for 1 hour, water and diethyl ether were added to the reaction mixture, and the organic layer was separated. The organic layer was washed with an aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure. The residue was purified by neutral silica gel column chromatography (heptane:ethyl acetate=30:1) to obtain the title compound (18 g, 0.52 mmol, 86%).

Provenance & Evidence