Sodium Hydroxide → HCID 22261122, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-{4-butyl-3-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid ethyl ester (0.12 g, 0.258 mmol) in ethanol (3 mL) was treated with 2 N aqueous NaOH (0.64 mL), and heated at 55° C. for 8 h. The reaction was cooled to ambient temperature and concentrated down to near dryness. The residue was then diluted with EtOAc (25 mL) and water (20 mL) and acidified to pH=1 with 1N aqueous HCl. The organic layer was washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to give a white solid (0.10 g, 88%). 1H NMR (400 MHz, CDCl3) δ 7.99-7.97 (m, 2H), 7.00 (d, J=7.8 Hz, 1H), 6.79 (d, J=2.0 Hz, 1H), 6.49 (dd, J=8.3, 2.0 Hz, 1H), 4.23 (t, J=7.6 Hz, 2H), 2.92 (t, J=7.6 Hz, 2H), 2.52 (t, J=7.6 Hz, 2H), 2.38 (s, 3H), 1.59 (s, 6H), 1.50 (quintet, J=7.8 Hz, 2H), 1.32 (sextet, J=7.5 Hz, 2H), 0.90 (t, J=7.3 Hz, 3H), MS (ES) m/e 438 (M+1).

Provenance & Evidence