Sodium Hydroxide → 5-(2-phenylpropyl)-1H-pyrazole-3-carboxylic Acid

Participants

Reaction Steps

Freshly prepared aq. NaOH (10 M in H2O, 1.01 mmol) was added to a stirring, room temperature solution of 61 (0.0523 g, 0.2024 mmol) in MeOH (0.51 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (9 min): The reaction was concentrated, redissolved in H2O, and extracted with EtOAc. 10% aq. HCl was added dropwise to the aqueous layer until the pH=2. When a white solid did not precipitate as expected, EtOAc was added, and the organic layer was removed, dried with Na2SO4, filtered, and concentrated to provide pure 62. 1H (CD3OD, 400 MHz): δ 7.24-7.18 (2H, m), 7.17-7.05 (3H, m), 6.56 (1H, s), 3.17 (1H, app sex, J=7.3 Hz), 2.96 (1H, dd, J=13.6, 7.3 Hz), 2.80 (1H, dd, J=13.7, 7.8 Hz), 1.25 (3H, d, J=6.8 Hz) ppm. 13C (CD3OD, 100 MHz): 6164.88, 153.40, 142.91, 140.97, 130.09, 129.25, 127.21, 106.11, 44.41, 34.96, 20.35 ppm. DEPT (CD3OD, 100 MHz): CH3 carbon: 20.35; CH2 carbon: 44.41; CH carbons: 130.09, 129.25, 127.21, 106.11, 34.96 ppm. HPLC: 8.849 min.

Provenance & Evidence