Tributylstannane → HCID 59259710, compound

Temperature

-78 °C

To a mixture of diisopropylamine (2.1 ml, 15 mmol) and tetrahydrofuran (30 ml) was added dropwise n-butyllithium (2.4M n-hexane solution, 5.0 ml, 12 mmol) at −78° C. (external temperature). Then, the reaction mixture was stirred for 30 minutes. To the mixture was added dropwise tributyltin hydride (3.3 ml, 12 mmol) at −78° C. (external temperature). Then, the reaction mixture was stirred at 0° C. (external temperature) for 40 minutes. After the reaction mixture was cooled at −78° C. (external temperature), to the reaction mixture was added dropwise 2-methoxyethoxymethyl chloride (1.4 ml, 12 mmol). After a temperature was raised to room temperature, to the reaction mixture were added diethyl ether and an aqueous ammonium chloride solution, and the organic layer was separated. The organic layer was washed with an aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure. The residue was purified by neutral silica gel column chromatography (heptane:ethyl acetate=20:1) to obtain the title compound (2.6 g, 6.9 mmol, 57%).

1. stirringThen, the reaction mixture was stirred at 0° C. (external temperature) for 40 minutes
2. temperatureAfter a temperature was raised to room temperature, to the reaction mixture
3. customan aqueous ammonium chloride solution, and the organic layer was separated
4. washThe organic layer was washed with an aqueous saturated sodium chloride solution
5. distillationthe solvent was distilled off under reduced pressure
6. customThe residue was purified by neutral silica gel column chromatography (heptane:ethyl acetate=20:1)

ORD record

ord-c8e9b8f9b6394f8fa3268c3e5eda276e

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696347B2