Tributylstannane → Stannane, tributyl(methoxymethyl)-

Participants

Reaction Conditions

Reaction Steps

To a mixture of diisopropylamine (9.4 mL) and THF (150 mL) was added n-butyl lithium (2.4M n-hexane solution, 25 mL) by drops at −78° C., which was stirred for 30 minutes at the same temperature. Tributyltin hydride (16 mL) was added dropwise to the reaction mixture at the same temperature, after which the reaction mixture was stirred for 30 minutes under ice cooling. The reaction solution was cooled to −78° C., then chloromethyl methyl ether (4.6 mL) was added dropwise thereto, and then which was gradually warmed to room temperature. Water (100 mL) and diethyl ether (300 mL) were added to the reaction solution, and the organic layer was washed with saturated brine, after which the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1) to obtain the titled compound (18 g).

Provenance & Evidence