Water → Stannane, trimethyl(4-methylphenyl)-

HRID 36184

Reaction equation

HRID 36184 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([Mg]Br)=[CH:3][CH:2]=1.[CH3:10][Sn:11](Cl)([CH3:13])[CH3:12].[Cl-].[NH4+].O>O1CCCC1>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([Sn:11]([CH3:13])([CH3:12])[CH3:10])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 25517Ammonium ChlorideHCID 178418370HCID 178418370, compound

Product 1

HCID 617834Stannane, trimethyl(4-methylphenyl)-Yield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d2abddd4026b4969baffadf398735ff2
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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