Isobutanol → Tributyl-(2-methylpropoxy)methyl-tin

Participants

Reaction Steps

To a mixture of sodium hydride (66%, 250 mg, 7.0 mmol) and tetrahydrofuran (20 ml) were added 2-methylpropanol (0.69 ml, 7.4 mmol) and N,N-dimethylformamide (20 ml) at 0° C. (external temperature). Then, the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture was added dropwise tributyl-iodomethyl-tin (2.0 g, 4.6 mmol) at 0° C. (external temperature). Then, the reaction mixture was stirred at room temperature for 5 hours and a half. To the reaction mixture were added heptane and water, 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 silica gel column chromatography (heptane:ethyl acetate=20:1) to obtain the title compound (1.7 g, 4.4 mmol, 95%).

Provenance & Evidence