Tributyltin Chloride → Trimethyl((tributylstannyl)ethynyl)silane

HRID 893704Notes

Reaction equation

HRID 893704 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[CH2:7]([Sn:11](Cl)([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH3:10]>O1CCCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]#[C:6][Sn:11]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 15096Tributyltin ChlorideHCID 66111Trimethylsilylacetylene

Product 1

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under argon stream, 3.53 ml (25 mmol) of trimethylsilylacetylene was dissolved in 25 ml of tetrahydrofuran and cooled to -78° C. Into the solution was added dropwise 14.9 ml (24 mmol) of butyllithiumhexane solution, and the reaction was carried out with stirring for 30 minutes. Then, 6.5 ml (24 mmol) of tributyltin chloride was added dropwise, and the reaction was carried out with stirring for 22 hours, while elevating gradually the temperature of the reaction mixture to room temperature. After the reaction, the solvent was evaporated and the residue was distilled under reduced pressure (0.6 mm Hg, 100°-102° C.) to obtain 4.84 g of a transparent liquid (yield: 52.2%).

Workup

  1. additionInto the solution was added dropwise 14.9 ml (24 mmol) of butyllithiumhexane solution
  2. stirringwith stirring for 22 hours
  3. customto room temperature
  4. customAfter the reaction
  5. customthe solvent was evaporated
  6. distillationthe residue was distilled under reduced pressure (0.6 mm Hg, 100°-102° C.)

Sources & evidence

ORD record
ord-97b779c108d74f16928f616bd8eb7ef9
Source dataset
uspto-grants-1992_06
Patent number
US05126361

Reaction notes

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