Tributylstannane → Stannane, tributyl(methoxymethyl)-

Temperature

-78 °C

To a mixture of diisopropylamine (9.4 mL, 67 mmol) and tetrahydrofuran (150 mL) was added dropwise n-butyl lithium (2.4 M n-hexane solution, 25 mL, 61 mmol) at −78° C., which was stirred for 30 minutes at the same temperature. Tributyltin hydride (16 mL, 61 mmol) was added dropwise to the reaction mixture at the same temperature, and stirred for 30 minutes at 0° C. The reaction mixture was cooled to −78° C., and chloromethyl methyl ether (4.6 mL, 61 mmol) was added dropwise thereto. The reaction mixture was gradually warmed to room temperature. Water was added to the reaction mixture, which was then extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:30) to obtain the title compound (18 g, 86%).

1. stirringstirred for 30 minutes at 0° C
2. temperatureThe reaction mixture was gradually warmed to room temperature
3. extractionwas then extracted with diethyl ether
4. washThe organic layer was washed with saturated aqueous sodium chloride
5. customthe solvent was evaporated under a reduced pressure
6. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:30)

ORD record

ord-d28709ce9e2f47a79c80b23e15321698

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507530B2