3-(4-chlorophenyl)-1-phenylpropan-1-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diethyl cyanomethylphosphonate (0.8 ml) was added dropwise at rt to a slurry of sodium hydride (60% in mineral oil, 0.2 g) in anhydrous 1,2-dimethoxyethane (15 ml) under nitrogen atmosphere. The reaction mixture was stirred at rt for 1 hour and 3-(4-chlorophenyl)-1-phenylpropan-1-one (0.4 g) was added. After stirring at 80° C. for 4 h the resultant solution was poured into ice water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4), and evaporated in vacuo. The crude mixture was separated by flash chromatography on silica gel (hexane/ethyl acetate 10:1) to afford (Z)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile (80 mg) and (E)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile (284 mg) as colourless oils. extracted with dichloromethane (3×20 ml) The combined organic layers were washed with brine (20 ml) dried (MgSO4) evaporated in vacuo The crude mixture was separated by flash chromatography on silica gel (hexane/ethyl acetate 10:1)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Silica gel (5.26 g) was added to a solution of 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (0.636 g) and 3,5-bis(ethoxycarbonyl)-1,4-dihydro-2,6-dimethylpyridine (1 g) in toluene (20 ml). The slurry was stirred at 70° C. in the dark for 17 h. After removal of the solvent the residue was purified by flash chromatography on silica gel (petrol ether/ethyl acetate) to provide 3-(4-chlorophenyl)-1-phenylpropan-1-one (0.49 g) as colourless solid. After removal of the solvent the residue was purified by flash chromatography on silica gel (petrol ether/ethyl acetate)