1,3-Diethyl-1,1,3,3-tetramethyldisilazane → Lithium bis(dimethylethylsilyl)amide

HRID 889792Notes

Reaction equation

HRID 889792 reaction equation
C([Li:5])CCC.[CH2:6]([Si:8]([NH:11][Si:12]([CH3:16])([CH3:15])[CH2:13][CH3:14])([CH3:10])[CH3:9])[CH3:7]>CCCCCC>[CH2:13]([Si:12]([N-:11][Si:8]([CH3:9])([CH3:10])[CH2:6][CH3:7])([CH3:15])[CH3:16])[CH3:14].[Li+:5]

Participants

4

Reactant 2

HCID 1403021,3-Diethyl-1,1,3,3-tetramethyldisilazaneHCID 178418339Butyllithium

Product 1

HCID 5128448Lithium bis(dimethylethylsilyl)amide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

Lithium bis(ethyldimethylsilyl)amide was prepared by the slow addition via syringe of a hexane solution of butyl lithium (50.6 mL of 2.73 M solution, 138 mmol) to a stirred hexane solution (100 mL) of bis(ethyldimethylsilyl)amine (26.2 g, 138 mmol) at room temperature. Stirring was continued for one hour and the solution was then refluxed for one hour. The hexane was evaporated under vacuum, leaving a pale yellow liquid. It was distilled at a temperature of 123° C. and a pressure of 0.2 torr to yield 23.2 g (86%) of clear liquid lithium bis(ethyldimethylsilyl)amide. Its viscosity was measured to be 37.5 centipoise at 40° C. Its NMR parameters are as follows:

Workup

  1. temperaturethe solution was then refluxed for one hour
  2. customThe hexane was evaporated under vacuum
  3. customleaving a pale yellow liquid
  4. distillationIt was distilled at a temperature of 123° C.

Sources & evidence

ORD record
ord-1e36c61fa6114ead93486d0ec4e78ad6
Source dataset
uspto-grants-2006_02
Patent number
US06994800B1

Reaction notes

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