Ethylenediaminetetraacetic Acid → 4-Methoxy-2-methylpyridine

Participants

Reaction Steps

Methylzinc chloride in THF (2 M, 10.489 mL, 21 mmol) was added to a solution of 2-chloro-4-methoxypyridine (0.500 g, 3.48 mmol) and Pd(PPh3)4 (0.161 g, 0.14 mmol) in THF (10 mL). The mixture was refluxed for 40 h and then poured into an aqueous solution (10 mL) containing ethylenediaminetetraacetic acid (1.5 g). The resulting mixture was neutralized with K2CO3 and extracted with Et2O. The organic layer was concentrated to give a residue, which was purified on a silica gel column eluting with MeOH:EtOAc (1:10) to give 4-methoxy-2-methylpyridine (0.213 g, 50.0%).

Provenance & Evidence