Tributylstannane → HCID 59259710, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of diisopropylamine (2.1 ml, 15 mmol) and tetrahydrofuran (30 ml) was added dropwise n-butyllithium (2.4M n-hexane solution, 5.0 ml, 12 mmol) at −78° C. (external temperature). Then, the reaction mixture was stirred for 30 minutes. To the mixture was added dropwise tributyltin hydride (3.3 ml, 12 mmol) at −78° C. (external temperature). Then, the reaction mixture was stirred at 0° C. (external temperature) for 40 minutes. After the reaction mixture was cooled at −78° C. (external temperature), to the reaction mixture was added dropwise 2-methoxyethoxymethyl chloride (1.4 ml, 12 mmol). After a temperature was raised to room temperature, to the reaction mixture were added diethyl ether and an aqueous ammonium chloride solution, 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=20:1) to obtain the title compound (2.6 g, 6.9 mmol, 57%).

Provenance & Evidence