Reaktion #64374

Reaktionsgleichung

water

p-Tolylmagnesium bromide

trimethyltin chloride

ammonium chloride

→

p-tolyltrimethyltin

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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 h 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 (39°-40 ° C., 0.1 mm Hg) which was further purified by flash chromatography (silica gel, hexane) to give p-tolyltrimethyltin as a colorless liquid.

Quelle