A solution of 2-chloropyridine (20.7 mL, 217 mmol) and trimethylchlorosilane (28.0 mL, 221 mmol) in THF (100 mL) was added dropwise to a rapidly stirred mixture of magnesium chips (6.75 g, 281 mmol) in THF (175 mL).
The solution in was added dropwise to a rapidly stirred mixture of magnesium shavings (6.75 g, 281 mmol) in THF (175 mL). After adding approximately 10 mL of
solution was followed by the addition of diiodomethane (0.2 mL), then iodine pellets, and then isopropylmagnesium chloride (2.0 M THF solution, 1 mL, 2
mmol). The suspension was then carefully heated to reflux and the remaining chloride solution was added dropwise over 2.75 hours. The reaction was then allowed to cool to room temperature and stirred overnight. Approximately 200 mL of was removed by distillation of the
THF and benzene (125mL) was added. The suspension was refluxed for 2 hours and the benzene was decanted. The benzene was then removed by adding more benzene (2 x 125 mL), refluxing (1 each time) and decanting.
hours) and decanting the process was repeated and the combined benzene fractions were concentrated in vacuum and distilled to give 2-trimethylsilylpyridine (6.97 g, 46.2 mmol , 21%) in colorless liquid form.
