ethyl 6-oxo-2-(trifluoromethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate

A mixture of ethyl 4, 4, 4-trifluoroacetoacetate (14.7 mL, 0.1 mol, 1.6 eq), acrylamide (4.5 g, 0.063 mol, 1.0 eq) and p-toluenesulphonic acid (0.156 g, 0.82 mmol, 0.013 eq) in toluene (60 mL) was refluxed for 38 h with azeotropic removal of water (Dean-Stark conditions). The reaction mixture was then concentrated to a small volume, by slow distillation of toluene at atmospheric pressure. Toluene (60 mL) was-added and again the reaction mixture was concentrated, through slow distillation of toluene. Afier repeating this operation three times, the reaction mixture was concentrated in vacuo and the solid residue was purified by flash chromatography (silica gel, eluent gradient: from hexane/ethyl acetate 9: 1 to hexane/ethyl acetate 8: 2). The title compound was obtained as a brownish solid (3.8 g, yield = 25percent). LC-MS (ESI+), MH+ : 238, 210, 190.; Description 33: 6-Hydroxy-2-trifluoromethyl-4, 5-dihydro-pyridine-3-carboxylic acid ethyl ester A mixture of ethyl 4, 4, 4-trifluoroacetoacetate (14.7 mL, 0.1 mol, 1.6 eq), acrylamide (4.5 g, 0.063 mol, 1.0 eq) and p-toluenesulphonic acid (0.156 g, 0.82 mmol, 0.013 eq) in toluene (60 mL) was refluxed for 38 h with azeotropic removal of water (Dean-Stark conditions). The reaction mixture was then concentrated to a small volume, by slow distillation of toluene at atmospheric pressure. Toluene (60 mL) was added and again the reaction mixture was concentrated, through slow distillation of toluene. After repeating this operation three times, the reaction mixture was concentrated in vacuo and the solid residue was purified by flash chromatography (silica gel, eluent gradient: from hexane/ethyl acetate 9: 1 to hexane/ethyl acetate 8: 2). The title compound was obtained as a brownish solid (3.8 g, yield = 25percent). LC-MS (ESI+), MH+ : 238, 210, 190.A mixture of ethyl 4, 4, 4-trifluoroacetoacetate (14.7 mL, 0.1 mol, 1.6 eq), acrylamide (4.5 g, 0.063 mol, 1.0 eq) and p-toluenesulphonic acid (0.156 g, 0.82 mmol, 0.013 eq) in toluene (60 mL) was refluxed for 38 h with azeotropic removal of water (Dean-Stark conditions). The reaction mixture was then concentrated to a small volume, by slow distillation of toluene at atmospheric pressure. Toluene (60 mL) was added and again the reaction mixture was concentrated, through slow distillation of toluene. After repeating this operation three times, the reaction mixture was concentrated in vacuo and the solid residue was purified by flash chromatography (silica gel, eluent gradient: from hexane/ ethyl acetate 9: 1 to [HEXANE/ETHYL] acetate 8: 2). The title compound was obtained as a brownish solid (3.8 g, yield = 25percent). LC-MS [(ESI+), ] MH+: 238, 210, 190.A mixture of ethyl 4, 4, 4-trifluoroacetoacetate (14.7 ml, 0.1 mol, 1.6 eq), acrylamide (4.5 g, 0.063 mol, 1.0 eq) and p-toluenesulphonic acid (0.156 g, 0.82 mmol, 0.013 eq) in toluene (60 ml) was refluxed for 38 h with azeotropic removal of water (Dean-Stark conditions). The reaction mixture was then concentrated to a small volume, by slow distillation of toluene at atmospheric pressure. Toluene (60 ml) was added and again the reaction mixture was concentrated, through slow distillation of toluene. After repeating this operation three times, the reaction mixture was concentrated in vacuo and the solid residue was purified by flash chromatography (silica gel, eluent gradient: from hexane/ethyl acetate 9:1 to hexane/ethyl acetate 8:2). The title compound was obtained as a brownish solid (3.8 g, yield = 25percent). LC-MS (ESI+), MH+: 238, 210, 190

Molecular Weight:237.18
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:237.06127767
Monoisotopic Mass:237.06127767
Topological Polar Surface Area:55.4
Heavy Atom Count:16
Complexity:346
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes