Water → Pyridine, 2-(trimethylstannyl)-

Temperature

-78 °C

Under an argon atmosphere, 7.5 ml of n-butyllithium (15% strength in hexane, 12 mmol) were added dropwise to a solution of 1.9 g (12.0 mmol) of 2-bromopyridine in 50 ml of absolute THF cooled to −78° C. After stirring at −78° C. for 1 h, 12 ml (12 mmol) of a 1 M solution of trimethyltin chloride in THF were added dropwise and the mixture was stirred at −78° C. for a further hour. The reaction solution was warmed to 0° C. and treated with water. The organic phase was separated off and the aqueous phase was extracted a number of times with diethyl ether. The combined organic phases were dried over sodium sulfate and concentrated. The residue was distilled in vacuo (0.3 bar) in a bulb tube. 1.9 g of the title compound resulted as a colorless oil.

1. stirringthe mixture was stirred at −78° C. for a further hour
2. temperatureThe reaction solution was warmed to 0° C.
3. customThe organic phase was separated off
4. extractionthe aqueous phase was extracted a number of times with diethyl ether
5. dry with materialThe combined organic phases were dried over sodium sulfate
6. concentrationconcentrated
7. distillationThe residue was distilled in vacuo (0.3 bar) in a bulb tube

ORD record

ord-cacf80bf109a4939a2ba868832cc0ce8

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06410573B1