Tetrabutylammonium Fluoride → HCID 58951441, compound

Participants

Reaction Steps

To a mixture of 2-(4-{4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-oxazol-2-yl}-phenoxymethyl)-pyridine (0.97 g, 1.76 mmol) in THF (20 mL) at 0° C. is added a solution of TBAF in THF (1.0 M, 1.76 mL). The mixture is warmed to room temperature and stirred for 2 h. The mixture is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc (3×). The combined organic phase is washed with brine (2×), dried (Na2SO4), and concentrated. The residue is purified by flash chromatography (SiO2, elute 0% to 10% MeOH/CH2Cl2) to yield 0.53 g of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.6 (dd, 1H), 7.8 (m, 3H), 7.6 (d, 1H), 7.4 (dd, 1H), 7.2 (d, 2H), 5.2 (s, 2H), 3.6 (t, 2H), 2.6 (t, 2H), 2.2 (s, 3H). MS (m/e) 311.1 (M+1)

Provenance & Evidence