Allyl bromide → HCID 20034695, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of lithium diisopropylamide (prepared from the addition of 38.2 ml of a 1.7M solution of tert.-butyl lithium in pentane to 9.53 ml of diisopropylamine in 100 ml of tetrahydrofuran at -10° C.) which was cooled to -78° C. was slowly added 24.1 g of the compound prepared in (c) above in 450 ml of tetrahydrofuran. The resultant mixture was then stirred for 45 minutes, while maintaining the temperature of -78° C., after which time it was cannulated into a solution of 159 ml of allyl bromide in 244 ml of tetrahydrofuran at -78° C. over a period of 90 minutes. The reaction mixture was then stirred for an additional 30 minutes at -78° C., after which time it was allowed to warm to room temperature. 150 ml of water was then added and the tetrahydrofuran was removed by evaporation at 40° C. The crude residue was then extracted with a mixture of ethyl acetate and water and dried, after which time the organic fraction was evaporated to yield a solid.

Provenance & Evidence