Tributyltin Chloride → Trimethyl((tributylstannyl)ethynyl)silane

HRID 345753Notes

Reaction equation

HRID 345753 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.CCCCCC.[CH2:18]([Sn:22](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>O1CCCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]#[C:6][Sn:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 66111TrimethylsilylacetyleneHCID 178418244HCID 178418244, compound

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 145.9 ml (24 mmol) of butyllithium-hexane 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. stirringwith stirring for 22 hours
  2. customto room temperature
  3. customAfter the reaction
  4. customthe solvent was evaporated
  5. distillationthe residue was distilled under reduced pressure (0.6 mm Hg, 100°-102° C.)

Sources & evidence

ORD record
ord-2bc65a1b6d944dbfb74c4b4570207870
Source dataset
uspto-grants-1991_10
Patent number
US05059590

Reaction notes

Loading…