Tetrahydrofuran → Dimethyl-(4-tributylstannylmethoxybutyl)amine

Temperature

45 °C

To a mixture of sodium hydride (72%, 232 mg, 7.0 mmol) and tetrahydrofuran (20 ml) was added 4-(dimethylamino)-1-butanol (0.82 g, 7.0 mmol) at 0° C. (external temperature), and the reaction mixture was stirred at 45° C. for 20 minutes. Then, the reaction mixture was cooled at 0° C. (external temperature). To the reaction mixture was added dropwise a mixture of tributyl-iodomethyl-tin (2.0 g, 4.6 mmol) and N,N-dimethylformamide (20 ml) at the same temperature. Then, the reaction mixture was stirred at 45° C. for 30 minutes. The reaction mixture was brought to room temperature, water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The organic layer was washed with water and an aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethylacetate=20:1, NH silica gel) to obtain the title compound (1.4 g, 3.3 mmol, 70%).

1. temperatureThen, the reaction mixture was cooled at 0° C. (external temperature)
2. additionTo the reaction mixture was added dropwise
3. stirringThen, the reaction mixture was stirred at 45° C. for 30 minutes
4. customwas brought to room temperature
5. customthe organic layer was separated
6. washThe organic layer was washed with water
7. distillationan aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure
8. customThe residue was purified by silica gel column chromatography (heptane:ethylacetate=20:1, NH silica gel)

ORD record

ord-f2badb7377a64c43a05925ac14f44cf8

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696347B2