Carbon Disulfide → Lithium Hexamethyldisilazide

Participants

Reaction Steps

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 were then added. The solution was allowed to warm to room temperature and evaporated to leave a yellow oil.

Provenance & Evidence