Acetic Anhydride → Lithium Hexamethyldisilazide

HRID 370505Notes

Reaction equation

HRID 370505 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(OCC2C=CC([N+]([O-])=O)=CC=2)=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 128496314-Nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)acetateHCID 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 by cannula to 1.57 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)acetate in 12 ml of dry THF at -78°, with stirring under argon. After 5 minutes 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 an orange oil.

Workup

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

Sources & evidence

ORD record
ord-c7851fd9a04c48c09e0d20d86bff637a
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

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