Tetrahydrofuran → HCID 14790773, compound

Participants

Reaction Steps

To stirred ethyl 2-oxo-phenylacetate (1.0 g, 5.6 mmol) under nitrogen atmosphere at ambient temperature was added trimethyl(trifluoromethyl)silane (1.0 mL, 6.73 mmol) and 1.0 TBAF in THF (6.2 mL, 6.2 mmol). This mixture was stirred at ambient temperature for 72 h. To the reaction was added 5N HCl solution (10 mL) and the mixture was stirred at ambient temperature for 18 h. The mixture was partitioned between Et2O and water. The Et2O layer was separated, dried over anhydrous Na2SO4, and filtered. Crude ethyl 2-phenyl-2-hydroxy-3,3,3-trifluoropropanoate was obtained as a yellow oil (0.9 g; HPLC RT=3.30 min, method A; 1H NMR, 400 MHz, CDCl3, 8.2 ppm (d, 1H), 7.78 ppm (m, 1H), 7.4 ppm (m, 3H), 4.4 ppm (m, 2H), 1.35 ppm (t, 3H)).

Provenance & Evidence