Hydrochloric Acid → HCID 123435007, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 140 ml (0.65 moles) of hexamethyldisilazane in 1.6 L of dry THF cooled to -78° C. was added 280 ml of a 2.5M solution of n-BuLi in hexane. The mixture was stirred and warmed to -5° C. over a 0.5 hour period. The siloxy ketone (192 g, 10.632 moles) was added as a solution in 100 ml of THF and stirred at -5° C. for 1 hour. This was then added to a solution of 200 ml (1.8 moles) of 80% propargyl bromide/toluene in 800 ml THF at -78° C. The mixture was warmed slowly to room temperature over a 1 hour period, then it was poured into cold dilute hydrochloric acid and extracted with ether. The ether extracts were combined, dried, filtered and concentrated to give 216 g of a light brown oil which was used immediately in the next reaction without further purification.

Provenance & Evidence