Triethyl 2-phosphonopropionate → HCID 54552716, compound

Participants

Reaction Steps

Triethyl 2-phosphonopropionate (0.61 g) is added to a solution of lithium diisopropylamide (from 0.32 g of diisopropylamine and 1.7 ml of 1.64M n-butyllithium) in 20 ml of dry tetrahydrofuran at 0° under nitrogen. After stirring at 0° for 15 minutes 5-(p-formylphenethyl)-imidazo[1,5-a]pyridine (0.55 g) is added in 5 ml of tetrahydrofuran and the reaction mixture is stirred for 1 hour at 0° and 1 hour at 25° before quenching with 25 ml of water. The layers are separated and the organic phase is dried and evaporated. The resulting oil is redissolved in ethyl acetate and passed through a column of silica gel to remove the excess phosphonate and to yield 5-[p-(2-ethoxycarbonylprop-1-enyl)phenethyl]imidazo[1,5-a]pyridine.

Provenance & Evidence