Diisopropylamine → 1-(Triethylsilyloxy)-1,2-bis(trimethylsilyloxy)ethene

HRID 1983548Notes

Reaction equation

HRID 1983548 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([Si:15](Cl)([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14].[CH3:21][Si:22]([O:25][C:26](=[O:33])[CH2:27][O:28][Si:29]([CH3:32])([CH3:31])[CH3:30])([CH3:24])[CH3:23]>C1COCC1>[CH2:13]([Si:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[O:33][C:26]([O:25][Si:22]([CH3:24])([CH3:23])[CH3:21])=[CH:27][O:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH3:14]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 13819ChlorotriethylsilaneHCID 118503Trimethylsilyl ((trimethylsilyl)oxy)acetateHCID 178418339Butyllithium

Product 1

HCID 601473361-(Triethylsilyloxy)-1,2-bis(trimethylsilyloxy)ethene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (15.5 mL, 0.11 mol) in THF (100 mL) at −78° C. was added a 1.6 M hexanes solution of n-butyl lithium (70 mL, 0.11 mol) over 15 minutes. After stirring for an additional 15 minutes at this temperature, triethylsilylchloride (16.7 mL, 0.1 mol) was added over 10 minutes followed by the addition of trimethylsilyl-2-(trimethylsiloxy)acetate (24.4 mL, 0.1 mol) over 30 minutes. The reaction was stirred at −78° C. for 30 minutes and warmed to ambient temperature by removing the cryogenic bath. The THF solvent was removed by vacuum rotary evaporation at 40° C. to precipitate out the lithium chloride. The mixture was taken up in 300 mL of hexanes and 5 mL of triethylamine and stirred for 5 min and the salt was allowed to settle. The supernatant was twice filtered through a pad of diatomaceous earth to give clear solution. The solution was concentrated under rotary evaporation to give the lightly yellow colored oil product as a mixture of geometrical isomers (4:1).

Workup

  1. additionwas added over 10 minutes
  2. temperaturewarmed to ambient temperature
  3. customby removing the cryogenic bath
  4. customThe THF solvent was removed by vacuum rotary evaporation at 40° C.
  5. customto precipitate out the lithium chloride
  6. stirring5 mL of triethylamine and stirred for 5 min
  7. filtrationThe supernatant was twice filtered through a pad of diatomaceous earth
  8. customto give clear solution
  9. concentrationThe solution was concentrated under rotary evaporation
  10. customto give the lightly yellow colored oil product
  11. additionas a mixture of geometrical isomers (4:1)

Sources & evidence

ORD record
ord-c4219e618b3b4a16be8a632d6b381fa5
Source dataset
uspto-grants-2009_06
Patent number
US07541458B2

Reaction notes

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