Sodium Hydroxide → HCID 11568313, compound

Participants

Reaction Steps

2-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzooxazole-6-carboxylic acid methyl ester (1.50 g, 3.32 mmol) in MeOH (10 mL) and THF (10 mL) is treated with NaOH (2.0 M, 20.0 mL). The resulting mixture is stirred at RT for 16 h. The mixture is concentrated, acidified with HCl (5 N) until pH˜3, and extracted with EtOAc (100 mL, then 50 mL). The organic layer is dried over Na2SO4, filtered, and concentrated to afford the title compound (1.40 g, 97%). H-NMR (ppm, CDCl3) δ: 8.16 (1H, d, J=1.3 Hz), 8.11 (1H, dd, J=1.3, 8.4 Hz), 7.78 (1H, d, J=8.4 Hz), 7.02 (1H, d, J=1.8 Hz), 6.97 (1H, dd, J=2.2, 8.4 Hz), 6.54 (1H, d, J=8.4 Hz), 4.85 (2H, s), 2.40 (2H, q, J=7.5 Hz), 2.30 (2H, q, J=7.5 Hz), 2.26 (3H, s), 1.25 (9H, s), 0.77 (6H, t, J=7.5 Hz). MS (ES) m/e: 438.2 (M+1), 436.2 (M−1).

Provenance & Evidence