Tributylstannane → Stannane, tributyl(methoxymethyl)-

Participants

Reaction Steps

n-Butyl lithium (2.4 M, n-hexane solution, 25 mL, 61 mmol) was dropped into a mixture of diisopropylamine (9.4 mL, 67 mmol) and tetrahydrofuran (150 mL) at −78° C. followed by stirring for 30 minutes at the same temperature. Tributyl tin hydride (16 mL, 61 mmol) was dropped in at the same temperature followed by stirring for 30 minutes while cooling with ice. The reaction mixture was brought to a temperature of −78° C. followed by dropping in chloromethyl methyl ether (4.6 mL, 61 mmol) and gradually warming to room temperature. Water (100 mL) was added to the reaction mixture followed by extraction with diethyl ether (300 mL). After washing the organic layer with sat. NaCl, the organic layer was distilled under a reduced pressure. The residue was purified by neutral silica gel column chromatography (heptane/ethyl acetate=30/1) to obtain the title compound (18 g, 0.52 mmol, 86%) as a colorless oil.

Provenance & Evidence