Tetrabutylammonium Fluoride → HCID 86594478, compound

Participants

Reaction Steps

Tetra-butyl ammonium fluoride (2.97 mL of a 1 M solution in THF, 2.97 mmol) was added to a solution of 2-benzyloxy-5-(2-trimethylsilyl-ethynyl)-benzoic acid benzyl ester (1.07 g, 2.58 mmol) in THF (10 mL) at room temperature. After 30 minutes, the mixture was diluted with ether (20 mL) and washed with water (3×30 mL) and brine (1×30 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (5% ethyl acetate/hexanes) to afford 687 mg (78%) product as a light orange oil. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, 1H, J=2 Hz); 7.52 (dd, 1H, J=9.1, 1 Hz); 7.38 (m, 10H); 6.95 (d, 1H, J=9.1 Hz); 5.35 (s, 2H); 5.19 (s, 2H); 3.0 (s, 1H).

Provenance & Evidence