Acetonitrile → 6-(2,4,6-Trimethylphenyl)-2-pyridineacetonitrile

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.5M, 19.1 mL, 47.8 mmol) was added to tetrahydrofuran (135 mL) and the solution was cooled to −78° C. Acetonitrile (2.5 mL, 47.8 mmol) was then added dropwise and the reaction stirred for 45 min. 2-Bromo-6-mesitylpyridine (2.00 g, 7.24 mmol) was added as a solution in 10 mL of tetrahydrofuran. The reaction continued to stir at −78° C. for 0.5 hr and was then warmed to room temperature for 1 h. The reaction was quenched with water and extracted with ethyl acetate, dried, and concentrated. Flash chromatography (20% ethyl acetate/hexanes) gave 0.70 g (41% yield) of the desired product as an orange oil.

Provenance & Evidence