Water → (S)-4-(1-(3-(3,5-dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl)ethyl)benzoic acid

Participants

Reaction Steps

Ethyl 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-(6-methoxy-2-naphthyl)-1H-pyrazol-1-yl]ethyl}benzoate (3.53 g, 6.48 mmol) was dissolved in MeOH-dioxane (1:1, 100 ml), and a solution of NaOH (1.2 g, excess)/water (10 ml) was added. The reaction was stirred at room temperature overnight. After concentrating the reaction mixture to 50 ml, it was acidified with 2N HCl and extracted with ethyl acetate. The organic layer was washed with brine 2× and dried over Na2SO4. Evaporation of solvent and vacuum drying gave 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-(6-methoxy-2-naphthyl)-1H-pyrazol-1-yl]ethyl}benzoic acid as a white powder. NMR (500 MHz, CDCl3) δ: 1.97 (d, J=7.0 Hz, 3H); 3.95 (s, 3H); 5.61 (q, J=7.0 Hz, 1H); 6.66 (s, 1H); 7.17 (d, J=2.5 Hz, H); 7.21 (dd, J=2.5, 9.0 Hz, 1H); 7.29 (dd, J=1.6, 8.4 Hz, 1H); 7.31 (t, J=1.9 Hz, 1H); 7.32 (d, J=8.4 Hz, 2H); 7.63 (d, J=1.6 Hz, 1H); 7.67 (d, J=9.0 Hz, 1H); 7.77 (d, J=8.4 Hz, 1H); 7.80 (d, J=1.9 Hz, 2H); 8.05 (d, J=8.4 Hz, 2H).

Provenance & Evidence