Sodium Hydroxide → HCID 11058026, compound

Participants

Reaction Steps

2-Methyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}propionic acid ethyl ester (6.4 g, 15.6 mmol) was dissolved in MeOH (200 mL) and 2N NaOH (150 mL) was added. The resulting cloudy solution became clear after 30 min and the reaction was stirred vigorously overnight. The solution was concentrated under reduced pressure, diluted with H2O (100 mL) and acidified to pH=1 with 5N HCl. The mixture was extracted with EtOAc (2×200 mL), dried (MgSO4), and concentrated under reduced pressure to provide a white solid. The compound was recrystallized from CH3CN (85 mL) to afford the product (4.50 g, 75%) as colorless needles after drying at 50° C. under vacuum for 6 h: Rf=0.14 in 35% EtOAc/hexanes; mp 129-130° C.; 1H NMR (400 MHz, CDCl3) δ 7.98-7.96 (m, 2H), 7.44-7.41 (m, 3H), 6.91-6.79 (m, 4H), 4.16 (t, J=8.8 Hz, 2H), 2.99 (t, J=8.8 Hz, 2H), 2.38 (s, 3H), 1.53 (s, 6H); 13C (100 MHz, CDCl3) δ 177.2, 159.7, 154.7, 148.3, 145.3, 132.4, 130.1, 128.7, 127.2, 126.1, 122.1, 114.9, 79.9, 67.0, 26.1, 25.1, 10.2; IR (CHCl3) 2991, 1775, 1718, 1554, 1506, 1469, 1237, 1145, 1023 cm−1; HRMS (TOF) m/e calcd. for C22H24NO5 (M++1) 382.1654, found 382.1628.

Provenance & Evidence