Methanol → 3-[3-(Tri-n-butylstannanyl)phenyl]pyridine

Participants

Reaction Steps

A cooled (−78° C.) solution of 3-(3-bromophenyl)pyridine (7.50 g, 32 mmol) in tetrahydrofuran (120 ml) was treated with a cooled (−78° C.) solution of tert-butyllithium (41 ml of a 1.7M solution in hexanes, 70 mmol). After 5 minutes tri-n-butyltin chloride (9.6 ml) was added and the mixture was allowed to warm to room temperature over 1 h. Methanol (7.5 ml) and triethylamine (7.5 ml) were added and the solvent evaporated. The residue was partitioned between ethyl acetate and saturated sodium hydrogencarbonate solution, the organics washed with brine, dried and evaporated to give a yellow oil. This oil was purified by silica gel flash column chromatography eluting with isohexane/ethyl acetate/triethylamine (99:1:0.5 through to 80:20:0.5) to afford 3-[3-(tri-n-butylstannanyl)phenyl]pyridine (11.7 g, 82%) as a colourless oil. 1H NMR (360 MHz, CDCl3) δH 0.86-0.93 (3H, m), 1.06-1.12 (2H, m), 1.28-1.40 (2H, m), 1.54-1.56 (2H, m), 7.34-7.39 (2H, m), 7.48-7.52 (2H, m), 7.62-7.65 (1H, m), 7.83-7.88 (1H, m), 8.57-8.60 (1H, m), 8.85 (1H, s).

Provenance & Evidence