Water → Bis(tributylstannyl)acetylene

HRID 380711Notes

Reaction equation

HRID 380711 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].O.[CH2:16]1[CH2:20]O[CH2:18][CH2:17]1>>[CH2:1]([Sn:5]([C:2]#[C:1][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:18][CH2:17][CH2:16][CH3:20])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 15096Tributyltin Chloride

Product 1

HCID 305981Bis(tributylstannyl)acetyleneYield 88%

Procedure

A mixture of 48.8 g (0.150 Mol) of tri-n-butyl-tin chloride and 20.7 g (0.225 Mol) of lithium acetylide ethylenediamine complex in 300 mL of anhydrous THF was heated at reflux under argon for 24 hr, cooled and treated with 200 mL of water. The layers were separated and the THF phase was suction-filtered through Celite with a 150 mL THF wash to afford a clear solution. This solution was washed with water (3×200 mL), saturated aqueous sodium bicarbonate (2×100 mL), 5% HCl (2×100 mL), and dried over anhydrous sodium sulfate. Removal of the solvent gave 40.2 g (88%) of the bis(tri-n-butylstannyl)ethyne as a colorless liquid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 24 hr
  3. temperaturecooled
  4. customThe layers were separated
  5. filtrationthe THF phase was suction-filtered through Celite with a 150 mL THF
  6. washwash
  7. customto afford a clear solution
  8. washThis solution was washed with water (3×200 mL), saturated aqueous sodium bicarbonate (2×100 mL), 5% HCl (2×100 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customRemoval of the solvent

Sources & evidence

ORD record
ord-2ee14700a4814ceca88d6e3048aac9da
Source dataset
uspto-grants-2001_10
Patent number
US06303733B1

Reaction notes

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