4-Methylpyridine → HCID 18446301, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 4-picoline (1.1 g, 11.8 mmol) in THF (5 mL) was added a solution of LDA 2M in THF/heptane/ethylbenzene (Aldrich) (5.9 mL, 11.8 mmol). The resulting reaction mixture was stirred at −78° C. for 3 h then −40° C. for 1 h. Cyclopropyl bromide (1.43 g, 11.8 mmol) was added at −78° C., the reaction mixture was allowed to warm up to room temperature and was stirred at room temperature for 1 h. To the reaction mixture was added saturated aqueous NH4Cl (10 mL), the aqueous phase was extracted with EtOAc (10×2 mL), and the combined organic extracts dried over Na2SO4. 4-Cyclopropylmethylpyridine-2-carboxylic acid (0.5 g, 31%) was obtained after the solvent was removed and used without further purification.

Provenance & Evidence