Carbon Disulfide → Lithium Hexamethyldisilazide

HRID 1980635Notes

Reaction equation

HRID 1980635 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(=S)=S.C(OC(=O)C)(=O)C>CCCCCC.C1COCC1.C(O)(=O)C>[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 6348Carbon DisulfideHCID 7918Acetic AnhydrideHCID 13838HexamethyldisilazaneHCID 178418339Butyllithium

Product 1

HCID 2733832Lithium Hexamethyldisilazide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 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 carbondisulphide 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-740318bccb4e4a6ea059b4ee9a740b8e
Source dataset
uspto-grants-1985_04
Patent number
US04510086

Reaction notes

Loading…