Tetrabutylammonium Fluoride → 2,8-Bis(trifluoromethyl)-alpha-(3-hydroxymethylphenyl)-4-quinolinemethanol

Participants

Reaction Steps

A solution of 2,8-bis(trifluoromethyl)-α-(3-tert-butyldimethylsilyloxymethylphenyl)-4-quinolinemethanol (crude, 1.17 mmol) in THF (5 mL) was treated with tetrabutylammonium fluoride (1-M in UHF, 0.7 mL, 0.7 mmol), stirred for 15 min, washed with water (2×2 mL), concentrated in vacuo and the resulting oil purified by chromatography [SiO2; heptane-EtOAc (3:1-1:1)] to give the title compound (117 mg, 25%) as a white solid: mp 152-154° C.; IR νmax (Nujol)/cm−1 3359, 3206, 2924, 1458, 1378, 1308, 1184, 1155, 1136, 1115, 1083, 1032, 766 and 695; NMR δH (400 MHz, CDCl3) 3.05 (1H, br s), 6.63 (2H, s), 6.48 (1H, s), 7.10-7.40 (4H, m), 7.68 (1H, m), 8.05-8.15 (2H, m), and 8.21 (1H, s).

Provenance & Evidence