Tributylstannane → Stannane, tributyl(methoxymethyl)-

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Reaction Steps

To a mixture of diisopropylamine (9.4 mL, 67 mmol) and tetrahydrofuran (150 mL) was added n-butyl lithium (2.4M n-hexane solution, 25 mL, 61 mmol) dropwise at −78° C., which was stirred for 30 minutes at the same temperature. Tributyltin hydride (16 mL, 61 mmol) was added dropwise at the same temperature, the solution was then stirred for 30 minutes on ice. The reaction solution was brought to −78° C., chloromethyl methyl ether (4.6 mL, 61 mmol) was added dropwise thereto, the solution was then gradually warmed to room temperature. Water (100 mL) was added to the reaction solution, which was then extracted with diethyl ether (300 mL). The organic layer was washed with brine, then, evaporated in vacuo. The residue was purified by neutral silica gel column chromatography (heptane/ethyl acetate=30/1), and the title compound (18 g, 0.52 mmol, 86%) was obtained as a colorless oil.

Provenance & Evidence