Triethyl 2-phosphonopropionate → HCID 54386781, 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 tetrahydrofuran at 0° under nitrogen. After stirring for 10 minutes, 5-(p-formylphenyl)-imidazo[1,5-a]pyridine (0.50 g) is added dropwise in a solution of 5 ml of tetrahydrofuran. The reaction mixture is stirred for two hours at 0° and quenched with 25 ml of water. The layers are separated and aqueous phase is extracted with ethyl acetate (2×10 ml). The organic phases are combined, dried over sodium sulfate, filtered and evaporated to yield an oil which is chromatographed on silica gel with ethyl acetate as eluent to yield 5-[p-(2-ethoxycarbonylprop-1-enyl)phenyl]imidazo[1,5-a]pyridine; IR (CH2Cl2) 1700 cm-1.

Provenance & Evidence