Sodium Hydroxide → HCID 22261093, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-{2-benzyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid ethyl ester (1.15 g, 2.30 mmol) in THF (15 mL) and MeOH (30 mL) was treated with 2.5N aqueous NaOH (10 mL). The solution was heated at 55° C. for 2 h, cooled to ambient temperature, and concentrated in vacuo. The residue was acidified with 5N aqueous HCl (5 mL) and partitioned between EtOAc (125 mL) and H2O (25 mL). The organic layer was washed with brine (50 mL), dried (Na2SO4), and concentrated to a colorless oil (1.1 g, 100%): 1H NMR (400 MHz, CDCl3) δ 7.97 (dd, 2H, J=7.6, 2.2 Hz), 7.44-7.40 (m, 3H), 7.27-7.15 (m, 5H), 6.77 (d, 1H, J=8.8 Hz), 6.69 (d, 1H, J=2.9 Hz), 6.62 (dd, 1H, J=8.8, 2.9 Hz), 4.12 (t, 2H, J=6.4 Hz), 3.93 (s, 2H), 2.96 (t, 2H, J=6.6 Hz), 2.35 (s, 3H), 1.45 (s, 6H); MS (ES) m/e 472 [M+1].

Provenance & Evidence