Lithium Hexamethyldisilazide → HCID 67322357, compound

Participants

Reaction Steps

To a solution of 15 g of 1-(4-chlorophenyl)-2-(methylthio)ethanone (2) in 70 mL of MTBE is added a solution of 86 mL of lithium hexamethyldisilazide (LiHMDS) under nitrogen gas, while keeping the temperature at −40° C. After stirring for 1.5 hours at this temperature, 14.4 g of ethyl 2-(1H-imidazol-1-yl)-2-oxoacetate (3) in 50 mL MTBE are added at 0° C., and the mixture is left stirring overnight at room temperature. The reaction solution was filtered off and the filtrate was suspended in 80 mL of MTBE. 50 mL of 6N HCl are added to the suspension. After separation of the phase by settling, the ether phase is washed 4 times with water and then concentrated under reduced pressure to obtain 22 g (73 mmol) of the title compound.

Provenance & Evidence