Hydrochloric Acid → (Z)-methyl 4-hydroxy-2-oxo-4-(phenanthren-3-yl)but-3-enoate

Participants

Reaction Steps

1-(4-(2-Aminoacetamido) phenyl)-N-isopropyl-5-(phenanthren-3-yl)-1H-pyrazole-3-carboxamide (15)Step a. To the mixture of 1-(phenanthren-3-yl)ethanone (1; 6.6 g, 30 mmol) and diethyl oxalate (2 ml) in MeOH (100 mL) was added sodium hydride (2.9 g, 120 mmol) portion-wise within 10 min. The reaction mixture was stirred at room temperature for 4 h, cooled down to 0° C. and acidified with 2N HCl. The precipitate was collected, washed with cold ethanol and dried to yield (Z)-methyl 4-hydroxy-2-oxo-4-(phenanthren-3-yl)but-3-enoate (1) as yellow crystal (7.3 g, 80%). It was used for the next step without further purification. 1H-NMR (300 MHz, DMSO-d6) δ 9.47 (s, 1H), 9.09 (d, J=7.8 Hz, 1H), 8.26 (d, J=9.0 Hz, 1H), 8.15 (d, J=9.0 Hz, 1H), 8.06-8.01 (m, 2H), 7.94 (d, J=7.8 Hz, 1H), 7.80-7.69 (m, 2H), 7.51 (s, 1H), 3.90 (s, 3H).

Provenance & Evidence