ethyl 2-oxo-3-phenylpropanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 39.3 g (0.08 mole) of pyrrolidone hydrotribromide (PHT) are introduced portionwise at approximately 10° C. into a solution of 13.9 g (0.072 mole) of ethyl 2-oxo-3-phenylpropanoate (described by E. L. Eliel et al. J. Org. Chem. 37, 505, 1972) in 250 ml of tetrahydrofuran (THF) and 6.1 g (0.072 mole) of 2-pyrrolidone. The temperature of the mixture is allowed to return to 20° C. and the mixture is then heated to 50° C. for 1 h. The mixture is cooled and then poured onto ice. The mixture is extracted with ether and the organic phase washed with water, dried with MgSO4, filtered and evaporated. 18 g of oil are obtained, which is used in the crude state for the next stage of the reaction. to return to 20° C. The mixture is cooled poured onto ice The mixture is extracted with ether the organic phase washed with water dried with MgSO4 filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of Example 1A (7.81 g, 40.7 mmol) and phenylhydrazine (4.00 mL, 40.7 mmol) was treated with concentrated sulfuric acid (4 drops), heated to 120° C. for 15 minutes, cooled to room temperature, treated with ethanol (50 mL), treated with bubbling HCl gas for 2 minutes, and heated to reflux for 1 hour. The mixture was poured into water (100 mL) and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was recrystallized from ethanol to provide 3.43 g (32%) of the desired product. cooled to room temperature heated to reflux for 1 hour extracted with diethyl ether The combined extracts were washed with water and brine dried (Na2SO4) filtered concentrated The concentrate was recrystallized from ethanol

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of Example 1A (7.81 g, 40.7 mmol) and phenylhydrazine (4.00 mL, 40.7 mmol) was treated with concentrated sulfuric acid (4 drops), heated to 120° C. for 15 minutes, cooled to room temperature, treated with ethanol (50 mL), treated with bubbling HCl gas for 2 minutes, and heated to reflux for 1 hour. The mixture was poured into water (100 mL) and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was recrystallized from ethanol to provide 3.43 g (32%) of the desired product. cooled to room temperature heated to reflux for 1 hour extracted with diethyl ether The combined extracts were washed with water and brine dried (Na2SO4) filtered concentrated The concentrate was recrystallized from ethanol

Conditions: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of diethyl oxalate (11.15 mL, 82.1 mmol) in diethyl ether (50 mL) at −78° C. was treated dropwise with 1 M benzylmagnesium chloride in diethyl ether (82 mL, 82 mmol) while maintaining an internal temperature of −60° C. The mixture was stirred for 30 minutes and poured into a mixture of concentrated HCl (8 mL), ice (40 mL), and diethyl ether (50 mL). The organic phase was washed with water and brine, dried (MgSO4), filtered, and concentrated to provide 15.5 g (98%) of the desired product of sufficient purity for subsequent use. The organic phase was washed with water and brine dried (MgSO4) filtered concentrated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 39.3 g (0.08 mole) of pyrrolidone hydrotribromide (PHT) are introduced portionwise at approximately 10° C. into a solution of 13.9 g (0.072 mole) of ethyl 2-oxo-3-phenylpropanoate (described by E. L. Eliel et al. J. Org. Chem. 37, 505, 1972) in 250 ml of tetrahydrofuran (THF) and 6.1 g (0.072 mole) of 2-pyrrolidone. The temperature of the mixture is allowed to return to 20° C. and the mixture is then heated to 50° C. for 1 h. The mixture is cooled and then poured onto ice. The mixture is extracted with ether and the organic phase washed with water, dried with MgSO4, filtered and evaporated. 18 g of oil are obtained, which is used in the crude state for the next stage of the reaction. to return to 20° C. The mixture is cooled poured onto ice The mixture is extracted with ether the organic phase washed with water dried with MgSO4 filtered evaporated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 39.3 g (0.08 mole) of pyrrolidone hydrotribromide (PHT) are introduced portionwise at approximately 10° C. into a solution of 13.9 g (0.072 mole) of ethyl 2-oxo-3-phenylpropanoate (described by E. L. Eliel et al. J. Org. Chem. 37, 505, 1972) in 250 ml of tetrahydrofuran (THF) and 6.1 g (0.072 mole) of 2-pyrrolidone. The temperature of the mixture is allowed to return to 20° C. and the mixture is then heated to 50° C. for 1 h. The mixture is cooled and then poured onto ice. The mixture is extracted with ether and the organic phase washed with water, dried with MgSO4, filtered and evaporated. 18 g of oil are obtained, which is used in the crude state for the next stage of the reaction. to return to 20° C. The mixture is cooled poured onto ice The mixture is extracted with ether the organic phase washed with water dried with MgSO4 filtered evaporated

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 3-phenylpyruvate (10 g; 0.052 mol) is dissolved in a mixture of acetonitrile (60 g) and trichlorotrifluoroethane (410 g), and the resulting solution is cooled to -10° C. Then, fluorine gas (0.067 mol) diluted with nitrogen to 10% concentration is introduced therein over a period of 2.5 hours while stirring vigorously. After addition of sodium fluoride (2 g), the solvent is distilled off under reduced pressure, and the residue is rectified to give ethyl 3-phenyl-3-fluoropyruvate (4.37 g). Boiling point, 90°-95° C./1 mmHg. is introduced the solvent is distilled off under reduced pressure

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1H-Benzoimidazol-5-ylamine (1 mmol) and 2,3,5 Trifluorobenzaldehyde (1 mmol) were added to ethanol (5 ml). After 30 min 2-Oxo-3-phenyl-propionic acid ethyl ester (1 mmol) was added. The reaction was heated to 50° C. and stirred for 24 h. After evaporation of the solvent the residue was purified with chromatographic methods. After evaporation of the solvent the residue was purified with chromatographic methods

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1H-Benzoimidazol-5-ylamine (1 mmol) and Quinoline-3-carbaldehyde (1 mmol) were added to ethanol (5 ml). After 30 min 2-Oxo-3-phenyl-propionic acid ethyl ester (1 mmol) was added. The reaction was heated to 50° C. and stirred for 24 h. After evaporation of the solvent the residue was purified with chromatographic methods. After evaporation of the solvent the residue was purified with chromatographic methods

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Imidazol-1-yl-propylamine (1 mmol) and 3-Hydroxy-benzaldehyde (1 mmol) were added to ethanol (5 ml). After 30 min 2-Oxo-3-phenyl-propionic acid ethylester (1 mmol) was added. The reaction was heated to 50° C. and stirred for 24 h. After evaporation of the solvent the residue was purified with chromatographic methods. After evaporation of the solvent the residue was purified with chromatographic methods