Acetic Anhydride → Lithium Hexamethyldisilazide

HRID 370500Notes

Reaction equation

HRID 370500 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(OC)=O)C(=O)C1)C=C.C(OC(=O)C)(=O)C>CCCCCC.C1COCC1.C(=S)=S>[CH3:6][Si:7]([CH3:14])([CH3:13])[N-:8][Si:9]([CH3:12])([CH3:11])[CH3:10].[Li+:5]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 13838HexamethyldisilazaneHCID 13578039HCID 13578039, compoundHCID 178418339Butyllithium

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 3

HCID 6348Carbon DisulfideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of lithium hexamethyldisilazide was prepared by the addition of 32.9 ml of a 1.6M solution of n-butyllithium in hexane to 11.25 ml of hexamethyldisilazane in 125 ml of dry THF at -10° with stirring, under argon. The solution was cooled to -78° and added to 5.0 g of methyl 2-(4-allylthioazetidin-2-on-1-yl)acetate in 60 ml of dry tetrahydrofuran at -78°, with stirring, under argon. After 5 min, 4.23 ml of carbon disulphide was added by syringe. 885 ml of acetic anhydride was then added. The solution were allowed to warm to room temperature and evaporated to leave a yellow oil.

Workup

  1. temperatureThe solution was cooled to -78°
  2. stirringwith stirring, under argon
  3. customevaporated
  4. customto leave a yellow oil

Sources & evidence

ORD record
ord-c1b25808bb8a47158ce43019585d4a18
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

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