Hexane → Lithium Hexamethyldisilazide

HRID 1952704Notes

Reaction equation

HRID 1952704 reaction equation
[CH3:1][Si:2]([NH:5][Si:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:3].C([Li:14])CCC.CCCCCC>CCOCC>[CH3:1][Si:2]([CH3:4])([CH3:3])[N-:5][Si:6]([CH3:9])([CH3:8])[CH3:7].[Li+:14]

Participants

5

Reactant 3

HCID 8058HexaneHCID 13838HexamethyldisilazaneHCID 178418339Butyllithium

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

An oven-dried 5 ml Schlenk flask was evacuated, purged with argon, and charged with 0.9 mol (0.689 g, 4.27 mmol) of bis(trimethylsilyl)amine followed by 5 ml of dry ether. The solution was cooled to 0° C. with an ice bath. To this solution was added n-butyllithium in hexane (2.4 ml of 1.6M, 3.84 mmol) dropwise. A white suspension was obtained. The ice bath was removed and the mixture was refluxed for 0.5 hours. After cooling to room temperature, the solvents were pumped off under vacuum to give a white crystalline solid of lithium hexamethyldisilazide (LiHMDS). To the solid was added 40 ml of dry toluene to obtain a clear colorless solution.

Workup

  1. customAn oven-dried 5 ml Schlenk flask was evacuated
  2. custompurged with argon
  3. customA white suspension was obtained
  4. customThe ice bath was removed
  5. temperaturethe mixture was refluxed for 0.5 hours
  6. temperatureAfter cooling to room temperature

Sources & evidence

ORD record
ord-69885fb84ab24b2c92f31943d27a2560
Source dataset
uspto-grants-2000_09
Patent number
US06114270

Reaction notes

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