Tetrahydrofuran → Diisopropylamine

Participants

Reaction Steps

A solution of the ketone 26a (60 mg) in THF (0.5 ml) is added at -78° C. to a solution of lithium diisopropylamide, obtained from diisopropylamine (0.024 ml) and n-butyllithium (0.084 ml of a 2 molar solution in hexane) in THF (0.5 ml). The temperature is brought back to -40° C. for 10 minutes. A solution of phenylselenyl bromide (40 mg) in THF (0.5 ml) is then added dropwise at -78° C. Water and ether are added. The organic phase is washed with water, bicarbonate and brine, and dried. After concentration under vacuum, the residue is purified on silica gel (ether/hexane, 1:9), to give 40 mg of selenide 32a (50% yield).

Provenance & Evidence