4-Toluenesulfonyl chloride → HCID 18511471, compound

Participants

Reaction Steps

A solution of 1-(2,8-bis(trifluoromethyl)-4-quinolinyl)-4-hydroxybutanol (176 mg, 0.5 mmol) in CH2Cl2 (5 mL) was treated with p-toluenesulphonyl chloride (102 mg, 0.55 mmol) and triethylamine (0.084 mL, 0.6 mmol) and stirred at room temperature for 16 h. The mixture was poured into saturated NaHCO3 solution (10 mL), extracted with CH2Cl2 (2×10 mL) and the combined organic phase dried (MgSO4), concentrated in vacuo, purified by chromatography [SiO2, heptane-EtOAc (95:5)] and the resulting solid triturated with cold hexane and filtered to give the title compound (111 mg, 66%) as a white solid: mp 61.0-61.7° C.; IR νmax (Nujol)/cm−1 3096, 2924, 2854, 1603, 1585, 1516, 1463, 1431, 1308, 1178, 1100, 1086 and 775; NMR δH (400 MHz, CDCl3) 1.79-1.86 (1H, m), 2.00-2.16 (2H, m), 2.63-2.71 (1H, m), 4.08 (1H, q, J 7.3 Hz), 4.24-4.29 (1H, m), 5.63 (1H, t, J 7.3 Hz), 7.72 (1H, t, J 7.7 Hz), 7.99 (1H, s), and 8.14-8.18 (2H, m).

Provenance & Evidence