Ethyl Acetate → HCID 22633471, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen, 2-[4-(2-{2-[4-(3,5-dimethyl-isoxazol-4-yl)-phenyl]-5-methyloxazol-4-yl}-ethoxy)-phenoxy]-2-methylpropionic acid ethyl ester (0.53 mmol) in ethanol (2.5 mL) and THF (2.5 mL) was treated with 2.0 N NaOH (2.0 mL). The reaction mixture was stirred at 55° C. for 1 h and concentrated in vacuo. The resulting slurry was suspended in ethyl acetate, acidified to pH 1 with 1 N HCl, and partitioned. The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo to provide the product in 86% yield. Rf=0.10 in 6:4 ethyl acetate:hexanes; 1H NMR (400 MHz, CDCl3) δ8.02 (d, J=8.8 Hz, 2H), 7.29 (d, J=8.8 Hz, 2H), 6.88 (d, J=8.8 Hz, 2H), 6.77 (d, J=8.8 Hz 2H), 4.17 (t, J=6.6 Hz, 2H), 2.97 (t, J=6.6 Hz, 2H), 2.41 (s, 3H), 2.37 (s, 3H), 2.77 (s, 3H), 1.50 (s, 6H); MS (EI) 499.2 (M+Na)+, 477.3 (M+H)+.

Provenance & Evidence