Tetrahydrofuran → 4-(2-Tributylstannylmethoxyethyl)morpholine

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium hydride (72%, 230 mg, 7.0 mmol) and tetrahydrofuran (20 ml) was added N-(2-hydroxyethyl)morpholine (843 μl, 6.96 mmol) at room temperature. Then, the reaction mixture was stirred at 45° C. (external temperature) for 20 minutes. To the reaction mixture was added tributyl-iodomethyl-tin (2.0 g, 4.64 mmol) at 0° C. (external temperature). Then, the mixture was stirred at 45° C. for 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added, and the organic layer was separated. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (NH silica gel, heptane:ethyl acetate=9:1) to obtain the title compound (1.7 g, 4.0 mmol, 85%).

Provenance & Evidence