Water → 6-Benzoxazoleethanol, 2-phenyl-

Participants

Reaction Steps

To the stirred solution of ethyl 2-(2-phenylbenzo[d]oxazol-6-yl)acetate (Daiichi Pharmaceuticals complay, Ltd, see EP1346982 A1, 2003)(407 mg, 1.37 mmol) in THF (12 mL) was added LAH at 10° C. The reaction mixture was allowed to stir at the same temperature for 2 h, water (0.07 mL), aqueous 15% NaOH (0.07 mL), and water (0.21 mL) were each carefully added to the mixture. The resulting slurry was filtered through a pad of Celite and concentrated in vacuo. The crude product was purified by flash column chromatography to afford the desired product as a clear gel (218 mg, 0.858 mmol, 63%). 1H NMR (DMSO-d6): 2.75 (t, 2H, J=7 Hz), 3.59 (q, 2H, J=7 Hz), 4.62 (t, 1H, J=5.2 Hz), 6.98 (t, 1H, J=7.4 Hz), 7.03 (dd, 1H, J=7.8 Hz, 1.2 Hz), 7.29-7.34 (m, 4H), 7.71 (d, 2H, J=7.6 Hz), 10.51 (s, 1H).

Provenance & Evidence