Trifluoroacetic acid → HCID 58415294, compound

Participants

Reaction Steps

Under argon at 24° C., crude benzofuran-5-yl(thiazol-2-yl)methanol (2.50 g, 10.8 mmol) was dissolved in 1,2-dichloroethane (40 mL), treated with triethylsilane (3.14 g, 27.0 mmol) and trifluoroacetic acid (1.25 mL, 16.2 mmol), and heated to reflux for 20 h. The mixture was diluted with EtOAc and ice, washed 1× with saturated aqueous NaHCO3, brine, dried over MgSO4, and evaporated. Purification by flash chromatography (hexanes to hexanes/EtOAc=3:2) gave 2-(benzofuran-5-ylmethyl)thiazole as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.71 (d, J=3.3 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.55 (br. s, 1H), 7.47 (d, J=8.4 Hz, 1H), 7.27-7.24 (m, 1H), 7.19 (d, J=3.3 Hz, 1H), 6.74-6.73 (m, 1H), 4.44 (s, 2H). MS (ESI) m/z: Calculated: 215.0; Observed: 216.1 (M++1).

Provenance & Evidence