Hexamethyldisilazane → Lithium Hexamethyldisilazide

HRID 484049Notes

Reaction equation

HRID 484049 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[Li:10]CCCC>C1COCC1>[CH3:1][Si:2]([N-:3][Si:4]([CH3:7])([CH3:6])[CH3:5])([CH3:9])[CH3:8].[Li+:10]

Participants

4

Reactant 2

HCID 13838HexamethyldisilazaneHCID 178418339Butyllithium

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of lithium bistrimethylsilylamide was prepared as follows. To hexamethyldisilazane (4.04 Kg, 5.28 L, 25 mol) was added anhydrous THF (4 L). The solution was cooled to -5° C. and n-BuLi (2.4M in hexanes, 9.7 L) was added over a period of 1.5 hr, while maintaining the reaction temperature between -5° and 0° C. The mixture was then aged for 10-15 min, allowed to rise to room temperature and stored under N2 overnight.

Workup

  1. temperaturewhile maintaining the reaction temperature between -5° and 0° C
  2. customto rise to room temperature
  3. waitstored under N2 overnight

Sources & evidence

ORD record
ord-27c33d4294b748a88dd7fb50528fa896
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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