Ethyl alpha-Formyl Benzeneacetic Acid Ester

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

Procedure: A solution of ethyl 3-oxo-2-phenylpropanoate (3.50 g, 18.2 mmol) and 4-bromoaniline (2.60 g, 15.1 mmol) in EtOH (25 mL) was stirred at room temperature overnight and concentrated to give the title compound as an oil. concentrated

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

Procedure: A solution of ethyl 3-oxo-2-phenylpropanoate (3.50 g, 18.2 mmol) and 4-bromoaniline (2.60 g, 15.1 mmol) in EtOH (25 mL) was stirred at room temperature overnight and concentrated to give the title compound as an oil. concentrated

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of crude 2-tert-butyl-5-cyclobutyl-2H-pyrazol-3-ylamine (1.0 g, 5.2 mmol) in AcOH (5 mL) was added 3-oxo-2-phenyl-propionic acid ethyl ester (1.0 g, 5.2 mmol). The reaction was then heated to 110° C. for 18 hr, at which time the reaction was cooled to room temperature, concentrated under reduced pressure to remove HOAc, diluted with EtOAc, and quenched with a saturated aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered through a fritted funnel, and concentrated under reduced pressure. Purification of the resulting material was accomplished by flash chromatography with a Biotage® 35L column (A Dynax Corp., Charlottesville, Va.), eluting with a gradient of 5%, 10%, 20% EtOAc/hexanes. The product was collected and concentrated under reduced pressure to give the title compound (15 mg, 9% yield). LRMS m/z (APCl) 322 (M+1). was cooled to room temperature concentrated under reduced pressure to remove HOAc diluted with EtOAc quenched with a saturated aqueous solution of NaHCO3 The organic layer was dried over MgSO4 filtered through a fritted funnel concentrated under reduced pressure Purification of the resulting material ), eluting with a gradient of 5%, 10%, 20% EtOAc/hexanes The product was collected concentrated under reduced pressure

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

Procedure: A solution of ethyl 3-oxo-2-phenylpropanoate (3.50 g, 18.2 mmol) and 4-bromoaniline (2.60 g, 15.1 mmol) in EtOH (25 mL) was stirred at room temperature overnight and concentrated to give the title compound as an oil. concentrated