2,2,2-Trifluoroethanol → HCID 86754668, compound

Participants

Reaction Conditions

Reaction Steps

A reaction mixture containing the trimethylsilyl derivative (28, 0.51 g, 1.74 mmol) in 10 mL of freshly distilled THF was treated with trifluoroethanol (0.18 g, 1.82 mmol) and tetrabutylammonium fluoride (1 M solution in THF, 1.74 mL, 1.74 mmol) at -78° C. under argon (FIG. 2E). The reaction mixture was allowed to stir at -78° C. for 20 min and at room temperature for 30 minutes. The reaction was quenched by the addition of water, followed by extraction with ethyl ether (2×15 mL). The combined organic extracts were washed with water, dried (MgSO4), filtered, and the solvent removed under vacuo. Silica gel chromatography (5% EtOAc:hexanes) gave the pure product as a colorless oil (270 mg, 71%). 1H NMR (CDCl3) δ 6.6-6.64 (m, 2H, ArH), 5.11 (s, 2H, CH2), 3.63 (s, 3H, CH3), 2.42 (s, 3H, CH3).

Provenance & Evidence