Tributylstannane → Tributyl(ethoxymethyl)stannane

Temperature

-78 °C

To a mixture of diisopropylamine (2.1 mL, 15 mmol) and tetrahydrofuran (30 mL) was added dropwise n-butyl lithium (2.4 M n-hexane solution, 5.0 mL, 12 mmol) at −78° C., and then the reaction mixture was stirred for 30 minutes. Tributyltin hydride (3.3 mL, 12 mmol) was added dropwise to this mixture at −78° C., and then the reaction mixture was stirred for 40 minutes at 0° C. The reaction mixture was cooled to −78° C., after which ethoxymethyl chloride (1.1 mL, 12 mmol) was added dropwise to the reaction mixture. The reaction mixture was raised to room temperature, diethyl ether and an ammonium chloride aqueous solution were added to the reaction mixture, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride, after which the organic layer was concentrated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (heptane:diethyl ether=30:1) to obtain the title compound (2.8 g, 66%).

1. stirringthe reaction mixture was stirred for 40 minutes at 0° C
2. temperatureThe reaction mixture was raised to room temperature
3. customthe organic layer was separated
4. washThe organic layer was washed with saturated aqueous sodium chloride
5. concentrationafter which the organic layer was concentrated under a reduced pressure
6. customThe residue was purified by neutral silica gel column chromatography (heptane:diethyl ether=30:1)

ORD record

ord-2876386ab7e34c46b93967f9972cba02

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158657B2