Tetrabutylammonium Fluoride → 2-Ethynyl-5-methylpyridine

Participants

Reaction Steps

To the solution of 5-methyl-2-((trimethylsilyl)ethynyl)pyridine (12-1) (4.16 g, 22 mmol) in THF was added tetra-n-butylammonium fluoride (44 mL, 44 mmol) at rt and the solution was stirred for 1 h. The solvent was removed under reduced pressure. The residue was purified by silca gel chromatography with eluent of PE/EA (20/1). The product was obtained as yellow oil (1.78 g, 69%). 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 7.46 (d, J=7.9 Hz, 1H), 7.38 (d, J=7.9 Hz, 1H), 3.10 (s, 1H), 2.35 (s, 3H); LRMS (ES) calculated M+H for C8H8N, 118.2. Found: 118.3.

Provenance & Evidence