(Trifluoromethyl)trimethylsilane → HCID 86730295, compound

Participants

Reaction Steps

To a solution of 2-(5-bromopyridin-2-yl)-2-methylpropanal (1.0 g, 4.4 mmol) and trimethyl(trifluoromethyl)silane (1.1 g, 7.5 mmol) in tetrahydrofuran (10 mL) under nitrogen was added the solution of TBAF (230 mg, 0.88 mmol) in tetrahydrofuran (5 mL) dropwise at −30° C. The resulting solution was stirred at −30° C. for 1 hour and at ambient temperature for an additional 1 hour before the addition of a second batch of TBAF (1.1 g, 4.4 mmol) at ambient temperature. After stirred at ambient temperature for 20 minutes, the reaction solution was diluted with water (10 mL), and then extracted with ethyl acetate (3×15 mL). All the organic solution was dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 2-5% ethyl acetate in hexane to afford the title compound as a yellow oil. MS ESI: [M+H]+ m/z 298, 300; 1H NMR (300 MHz, CDCl3) δ 8.55 (s, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.24 (d, J=8.7 Hz, 1H), 4.01 (q, J=7.8 Hz, 1H), 1.51 (s, 6H).

Provenance & Evidence