反应详情

p-Tolylmagnesium bromide solution (Aldrich) (1.0M solution in diethyl ether) (53 ml, 0.0530 mol) was added dropwise to trimethyltin chloride (6.92 g, 0.0347 mol) in tetrahydrofuran (50 ml) under nitrogen at -10° C. The suspension was allowed to warm slowly to room temperature over 3 hours then saturated ammonium chloride solution (10 ml) was added followed by sufficient water to dissolve the precipitate. The solution was extracted three times with diethyl ether-hexane (1:1). The combined organic phase was washed with brine, dried (magnesium sulfate) and the solvents removed in vacuo. Vacuum distillation of the residue afforded a colorless liquid (bp 39°-40° C., 0.1 mm Hg) which was further purified by flash chromatography (silica gel, hexane) to give p-tolyltrimethyltin (7.30 g, 82%) as a colorless liquid; 1H NMR (300 MHz, CDCl3) δ7.40 (d, J=7.7 Hz, 2H), 7.19 (d, J=7.7 Hz, 2H), 2.34 (s, 3 H), 0.30 (s, 9H).

1. dissolutionto dissolve the precipitate
2. extractionThe solution was extracted three times with diethyl ether-hexane (1:1)
3. washThe combined organic phase was washed with brine
4. dry with materialdried (magnesium sulfate)
5. customthe solvents removed in vacuo
6. distillationVacuum distillation of the residue
7. customafforded a colorless liquid (bp 39°-40° C., 0.1 mm Hg) which
8. customwas further purified by flash chromatography (silica gel, hexane)