Tetrahydrofuran → Tributyl-cyclobutoxymethyl-tin

Participants

Reaction Steps

To a mixture of sodium hydride (66%, 250 mg, 7.0 mmol) and tetrahydrofuran (20 ml) were added cyclobutanol (0.55 ml, 7.0 mmol) and N,N-dimethylformamide (20 ml) at 0° C. (external temperature). Then, the reaction mixture was stirred at room temperature for 40 minutes. 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 overnight. 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 then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethylacetate=20:1) to obtain the title compound (1.6 g, 4.3 mmol, 92%).

Provenance & Evidence