Water → HCID 18511433, compound

Participants

Reaction Steps

A solution of α-phenyl-2,8-bis(trifluoromethyl)quinoline-4-methanol (50 mg, 0.13 mmol) in anhydrous THF (4 mL) was treated with NaH (18 mg, 60% dispersion in oil, 0.44 mmol), stirred at room temperature for 2 min, treated with iodomethane (0.8 mL, 1.2 mmol) and stirred for 15 min. The solution was then treated with water (10 mL), extracted with ether (2×10 mL), the extracts washed with water (10 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; heptane-EtOAc (10:1)] to give the title compound (41 mg, 79%) as a pale solid: mp 115-117° C.; IR νmax (liquid film)/cm−1 3070, 2929, 2854, 1589, 1588, 1517, 1491, 1456, 1429, 1378, 1210, 1276, 1211, 1184, 1164, 1129 and 1101; NMR δH (400 MHz, CDCl3) 3.47 (3H, s), 5.90 (1H, s), 7.29-7.35 (5H, m), 7.60-7.64 (1H, t J 8 Hz) and 8.25 (1H, d J 8 Hz).

Provenance & Evidence