Allyl bromide → HCID 69683505, compound

Participants

Reaction Conditions

Reaction Steps

70 cm3 of a solution of butyllithium in hexane (2.5M concentration) were added, with stirring and under an inert atmosphere, to 150 cm3 of tetrahydrofuran cooled to a temperature in the region of −70° C., followed by addition of 50 cm3 of tetrahydrofuran and 23 cm3 of diisopropylamine predissolved in 300 cm3 of tetrahydrofuran. After a further addition of 50 cm3 of tetrahydrofuran, the mixture was stirred for 15 minutes at about −70° C., followed by addition of 45.15 g of ethyl de 1-(tert-butyloxycarbonyl)isonipecotate predissolved in 400 cm3 of tetrahydrofuran, and finally 50 cm3 of this same solvent. After stirring the mixture for 1 hour at a temperature in the region of −70° C., 16.7 cm3 of allyl bromide predissolved in 150 cm3 of tetrahydrofuran were added and the mixture was then warmed to about 20° C. and stirred for 17 hours. The mixture was poured into 200 cm3 of saturated aqueous ammonium chloride solution and then extracted with about 2 liters of ethyl acetate.

Provenance & Evidence