Hexamethyldisilazane → Lithium Hexamethyldisilazide

HRID 383227Notes

Reaction equation

HRID 383227 reaction equation
[Li:1]CCCC.[CH3:6][Si:7]([CH3:14])([CH3:13])[NH:8][Si:9]([CH3:12])([CH3:11])[CH3:10].[NH4+].[Cl-]>C1COCC1>[CH3:6][Si:7]([CH3:14])([CH3:13])[N-:8][Si:9]([CH3:12])([CH3:11])[CH3:10].[Li+:1]

Participants

5

Reactant 3

HCID 13838HexamethyldisilazaneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of lithiumhexamethyl disilazide was prepared by adding 4.8 ml of 1.6 m BuLi in hexanes to a solution of 1.8 ml of hexamethyldisilazane in 10 ml of dry THF at −40° C. This solution was stirred for 15 min at −40° C. A quantity of 7.8 ml of this solution was added dropwise to a solution of 1.34 g of compound 13 in 20 ml of dry THF at −70° C. The mixture subsequently stirred at −70° C. for an additional hr and then poured into 50 ml of sat. NH4Cl solution and extracted with ethyl acetate.

Workup

  1. stirringThe mixture subsequently stirred at −70° C. for an additional hr
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-4447b5e2032b404f84f2158865148544
Source dataset
uspto-grants-2013_02
Patent number
US08367648B2

Reaction notes

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