Tetrahydrofuran → 4-(2-Tributylstannylmethoxyethyl)morpholine

Temperature

45 °C

To a mixture of sodium hydride (72%, 230 mg, 7.0 mmol) and tetrahydrofuran (20 ml) was added N-(2-hydroxyethyl)morpholine (843 μl, 6.96 mmol) at room temperature. Then, the reaction mixture was stirred at 45° C. (external temperature) for 20 minutes. To the reaction mixture was added tributyl-iodomethyl-tin (2.0 g, 4.64 mmol) at 0° C. (external temperature). Then, the mixture was stirred at 45° C. for 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added, and the organic layer was separated. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (NH silica gel, heptane:ethyl acetate=9:1) to obtain the title compound (1.7 g, 4.0 mmol, 85%).

1. stirringThen, the mixture was stirred at 45° C. for 30 minutes
2. temperatureAfter the reaction mixture was cooled to room temperature
3. customthe organic layer was separated
4. washThe organic layer was washed with an aqueous saturated sodium chloride solution
5. dry with materialdried with anhydrous sodium sulfate
6. distillationAfter the solvent was distilled off under reduced pressure
7. customthe residue was purified by silica gel column chromatography (NH silica gel, heptane:ethyl acetate=9:1)

ORD record

ord-cb5b155b46b04045a049c9a04d1c54f1

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696347B2