Diisopropylamine → HCID 23325187, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 17.6 g of 1B in 300 ml of dry tetrahydrofuran was added drop-by-drop to a solution of lithium diisopropylamide (prepared by adding 38 ml of a 2.2M solution of n-butyllithium in hexane to a solution of 11 ml of diisopropylamine and 12 ml of tetramethylethylenediamine in 450 ml of tetrahydrofuran) at -78° C. under argon. The resulting solution was held at -78° C. for 40 minutes, then a solution of 13.5 ml of tert-butyl bromoacetate in 50 ml of dry tetrahydrofuran was added. The resulting mixture was stirred at -78° C. for 30 minutes, at 0° C. for 10 minutes, then was poured into 300 ml of ice water containing 4.5 g of ammonium chloride. The resulting mixture was extracted with ether, the extract was washed with water, treated with charcoal and the solvent was evaporated. The residue was stirred in a solution of 7.5 g of sodium methoxide in 700 ml of methanol for 24 hours at room temperature. Then the solvent was evaporated and the residue was mixed with 200 ml of water containing 7.5 g of ammonium chloride. The mixture was extracted with ether, the extract was washed with water, dried (MgSO4) and the solvent was evaporated to give tert-butyl 3-(benzylideneamino)-4-pentynoate (5A), as a brown oil.

Provenance & Evidence