Hexane → Lithium Hexamethyldisilazide

HRID 485119Notes

Reaction equation

HRID 485119 reaction equation
C([Li:5])CCC.CCCCCC.[CH3:12][Si:13]([CH3:20])([CH3:19])[NH:14][Si:15]([CH3:18])([CH3:17])[CH3:16]>>[CH3:12][Si:13]([CH3:20])([CH3:19])[N-:14][Si:15]([CH3:18])([CH3:17])[CH3:16].[Li+:5]

Participants

4

Reactant 3

HCID 8058HexaneHCID 13838HexamethyldisilazaneHCID 178418339Butyllithium

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Procedure

A solution of n-butyllithium in hexane (1.55M, 390 ml, 0.605 moles) is cooled to 0° C. and treated dropwise over a period of 15 min with neat hexamethyldisilazane (118.12 g, 0.7337 moles). The resulting yellow solution is then refluxed for 1.5 hr, and concentrated in vacuo to yield a white solid residue. To remove the excess hexamethyldisilazane, this residue is dissolved in heptane, and the heptane is removed in vacuo. The material is then tumble-dried (50° C./2 mm/30 min). The final product is a white solid with a melting point of 70°-83° C.

Workup

  1. temperatureThe resulting yellow solution is then refluxed for 1.5 hr
  2. concentrationconcentrated in vacuo
  3. customto yield a white solid residue
  4. customTo remove the excess hexamethyldisilazane
  5. dissolutionthis residue is dissolved in heptane
  6. customthe heptane is removed in vacuo
  7. customThe material is then tumble-dried (50° C./2 mm/30 min)

Sources & evidence

ORD record
ord-c826a6adbb5043bf8ffff80345c1f6d2
Source dataset
uspto-grants-1985_08
Patent number
US04535173

Reaction notes

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