تفاعل #64462

معادلة التفاعل

water

p-Tolylmagnesium bromide

trimethyltin chloride

ammonium chloride

→

p-tolyltrimethyltin

المردود 82.5%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.DISSOLUTIONto dissolve the precipitate
2. 2
   استخلاصThe solution was extracted three times with diethyl ether-hexane (1:1)
3. 3
   غسيلThe combined organic phase was washed with brine
4. 4
   تجفيفdried (magnesium sulfate)
5. 5
   أخرىthe solvents removed in vacuo
6. 6
   workup.DISTILLATIONVacuum distillation of the residue
7. 7
   أخرىafforded a colorless liquid (bp 39°-40° C., 0.1 mm Hg) which
8. 8
   أخرىwas further purified by flash chromatography (silica gel, hexane)

الإجراء التجريبي

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, 3H), 0.30 (s, 9H).

المصدر