Trimethyltin chloride → HCID 22000199, compound

Participants

Reaction Steps

A solution of t-butyllithium (1.7M in pentane; 8.5 ml, 14.45 mmol) was added dropwise to a stirred solution of 3-methoxy-6-trifluoromethylpyridine (1.57 g, 8.87 mmol) in dry tetrahydrofuran (20 ml) at −78° C. over 5 min. After stirring for 10 min at −78° C. a solution of trimethyltin chloride in tetrahydrofuran (18 ml, 1 M in THF, 18 mmol) was added over 5 min. The reaction mixture was allowed to warm up to room temperature over 5 hour and then quenched with water (50 ml) and extraxted with hexane (3×30 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (100 g, hexane:diethyl ether 0-10%) to afford 3-methoxy-6-trifluoromethyl-2-trimethystannylpyridine (0.7 g, 23%) H1 NMR δ(250 MHz, CDCl3): 7.50 (1H, d, J 8.7 Hz), 7.02 (1H, d, J 8.7 Hz), 3.85 (3H, s), 0.35 (9H, s); and afford 3-methoxy-6-trifluoromethyl-4-trimethylstannylpyridine (1.7 g, 57%) H1 NMR δ(250 MHz, CDCl3): 8.38 (1H, s), 7.65 (1H, s), 3.95 (3H, s) 0.35 (9H, s).

Provenance & Evidence