Sodium amide → HCID 10026043, compound

Participants

Reaction Steps

11.7 g (0.3 mol) sodium amide are suspended in 300 ml tetrahydrofurane under nitrogene. 71.47 g (0.3 mol) triethyl 2-phosphonopropionate are dropped to the stirred mixture which is kept at ambient temperature for 2 hours subsequently. 30.5 g (86.5 mmol) 1-(1-triphenylmethyl-1H-imidazol-4-yl)ethanone are added and the mixture is held under reflux for 16 hours. Evaporation and dissolving in 1 l chloroform/2-propanol (3:1) is follwed by washing 3 times with water. Drying with sodium sulphate and evaporation result an oil which mainly consists of E-ethyl 2-methyl-3-(1-triphenylmethyl-1H-imidazol-4-yl)2-butenate. Treating this residue with diethyl ether affords 10.9 g of a solid material mainly consisting of the Z-isomer. Purification via column chromatography (silicagel 63-200 μm, eluent: petrol ether/diethyl ether [2:2]) leads to 5.6 g (14.8%) of the title compound as a white solid. An analytical sample was recrystallized from diethyl ether/ethanol resulting colourless crystals, melting point 166°-168° C.

Provenance & Evidence