ethyl 3-anilino-2-methyl-3-oxopropanoate

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

Procedure: Prepared according to Procedure B using ethyl 2-methyl-3-oxo-3-(phenylamino)-propanoate (8.60 g, 39 mmol) and sodium hydroxide (2.00 g, 50 mmol) in THF (40.00 mL), water (10.00 mL, 555 mmol) and MeOH (10.00 mL) to afford product as a colorless solid, which was used without further purification. Mass Spectrum (ESI) m/e=192.1 [M−1]. Prepared to afford product as a colorless solid, which was used without further purification

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

Procedure: Prepared according to Procedure A using diethyl 2-methylmalonate (24.485 g, 141 mmol), aniline (9.00 mL, 99 mmol) and pyridine (16 mL) to afford product as a colorless oil after purification by chromatography on silica gel, eluting with EtOAc gradient in hexane. 1H NMR (400 MHz, chloroform-d) δ ppm 8.66 (1H, br. s.), 7.55 (2H, d, J=7.8 Hz), 7.33 (2H, t, J=8.0 Hz), 7.13 (1H, t, J=7.4 Hz), 4.20-4.33 (2H, m), 3.46 (1H, q, J=7.2 Hz), 1.56 (3H, d, J=7.4 Hz), 1.26-1.39 (3H, m). Prepared to afford product as a colorless oil after purification by chromatography on silica gel eluting with EtOAc gradient in hexane