Chlorotrimethylsilane → 1,1-Bis(trimethylsilyl)ethanol

HRID 396108Notes

Reaction equation

HRID 396108 reaction equation
[CH3:1][Si:2]([CH3:5])([CH3:4])Cl.[Na].[CH3:7][Si:8]([CH2:11][C:12]([O-])=O)([CH3:10])[CH3:9].[O:15]1CCCC1>>[CH3:7][Si:8]([CH3:10])([CH3:9])[C:11]([Si:2]([CH3:5])([CH3:4])[CH3:1])([OH:15])[CH3:12]

Participants

5

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028Tetrahydrofuran2×HCID 5360545SodiumHCID 225582202-Trimethylsilylacetate

Product 1

HCID 153512391,1-Bis(trimethylsilyl)ethanolYield 55%

Conditions

Temperature
80 °C

Procedure

Trimethylchlorosilane (20.5 g, 190 mmol) is dissolved in 30 mL of tetrahydrofuran. The solution is suspended with sodium (6.50 g, 283 mmol) and then refluxed at 80° C. Under the argon atmosphere, trimethylsilylacetate (3.12 g, 23.6 mmol) in 20 mL of tetrahydrofuran is added via a syringe for an hour and then the solution is refluxed for another 30 minutes. Then, precipitated inorganic residue is filtered and solvent is removed under vacuum. Remained oil is separated by vacuum distillation to give 1,1-bis(trimethylsilyl)ethanol (yield: 55%). b.p. 110° C. (24 mmHg).

Workup

  1. temperaturethe solution is refluxed for another 30 minutes
  2. customThen, precipitated inorganic residue
  3. filtrationis filtered
  4. customsolvent is removed under vacuum
  5. customRemained oil is separated by vacuum distillation

Sources & evidence

ORD record
ord-f5616dcb27df401e81aec92627aa898a
Source dataset
uspto-grants-2003_08
Patent number
US06607867B1

Reaction notes

Loading…