Hexamethyldisilazane → Lithium Hexamethyldisilazide

HRID 370502Notes

Reaction equation

HRID 370502 reaction equation
C([Li:5])CCC.[CH3:6][Si:7]([CH3:14])([CH3:13])[NH:8][Si:9]([CH3:12])([CH3:11])[CH3:10].C(SC1N(CC(OCOC(=O)C(C)(C)C)=O)C(=O)C1)C=C>CCCCCC.O1CCCC1>[CH3:6][Si:7]([CH3:14])([CH3:13])[N-:8][Si:9]([CH3:12])([CH3:11])[CH3:10].[Li+:5]

Participants

6

Reactant 3

HCID 13838HexamethyldisilazaneHCID 13578041HCID 13578041, compoundHCID 178418339Butyllithium

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of lithium hexamethyldisilazide was prepared by the addition of 3.53 ml of a 1.6M solution of n-butyllithium in hexane to 1.19 ml of hexamethyldisilazane in 25 ml of dry tetrahydrofuran at -10° with stirring under argon. The solution was cooled to -78° and added by cannula to 1.02 g of pivaloyloxymethyl 2-(4-allylthioazetidin-2-on-1-yl)acetate in 10 ml of dry tetrahydrofuran at -78° with stirring under argon.

Workup

  1. temperatureThe solution was cooled to -78°
  2. stirringwith stirring under argon

Sources & evidence

ORD record
ord-c3a3ec5ff0394a0ea71072afd16412fe
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

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