Acetic Anhydride → Lithium Hexamethyldisilazide

HRID 370499Notes

Reaction equation

HRID 370499 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(O)(=O)C.C(=S)=S>[CH3:6][Si:7]([CH3:14])([CH3:13])[N-:8][Si:9]([CH3:12])([CH3:11])[CH3:10].[Li+:5]

Participants

9

Reactant 4

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

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6348Carbon DisulfideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of lithium hexamethyldisilazide was prepared by the addition of 5.12 ml of a 1.6M solution of n-butyllithium in hexane to 1.75 ml of hexamethyldisilazane in 25 ml of dry THF at -10° with stirring, under argon. The solution was cooled to -78° and added to 1.0 g of methyl 2-(4-allylthioazetidin-2-on-1-yl)acetate in 12 ml of dry tetrahydrofuran at -78°, with stirring, under argon. After 5 min, 0.846 ml of carbon disulphide was added by syringe. 1.77 ml of acetic anhydride were then added, followed by 1.07 ml of glacial acetic acid. The solution was 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-3a895bd3c86244d9a069d2010d857a80
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

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