Trimethylsilylacetylene → HCID 101337817, compound

HRID 1849933Notes

Reaction equation

HRID 1849933 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[CH:12]([SiH:15]([CH:17]([CH3:19])[CH3:18])Cl)([CH3:14])[CH3:13]>CCCCC>[CH:12]([SiH:15]([CH:17]([CH3:19])[CH3:18])[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 2758383Chlorodi(isopropyl)silaneHCID 178418339Butyllithium

Product 1

HCID 101337817HCID 101337817, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A flame-dried 250-mL round-bottom flask was cooled under nitrogen and placed in an ice bath. Into this flask was added 30 mL pentane and 3.6 g (36 mmol) trimethylsilylacetylene. n-Butyllithium (13.2, 2.5 M in hexane) was added over 12 minutes, and the reaction was allowed to stir for one hour at 0° C. Diisopropylchlorosilane (5.1 g, 34 mmol) was then added, and the reaction stirred overnight. The solution was extracted with pentane (2×40 mL) and the organic layers were washed with water, dried over magnesium sulfate, filtered, then carefully concentrated using rotary evaporation (product was volatile). Chromatography on silica with pentane as an eluent yielded 6.9 g (33 mmol, 99%) the desired product as a clear oil.

Workup

  1. temperatureA flame-dried 250-mL round-bottom flask was cooled under nitrogen
  2. customplaced in an ice bath
  3. stirringthe reaction stirred overnight
  4. extractionThe solution was extracted with pentane (2×40 mL)
  5. washthe organic layers were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationcarefully concentrated
  9. customevaporation (product was volatile)

Sources & evidence

ORD record
ord-b26a39441367431488277b8134aa3a6b
Source dataset
uspto-grants-2015_02
Patent number
US08956555B2

Reaction notes

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