(Trifluoromethyl)trimethylsilane → HCID 69083891, compound

Participants

Reaction Steps

A mixture of the aldehyde (95) (3.0 g, 7 mmol) (Prepared according to the synthesis of Example 149 step 3) TBAF (1.06 g, 3 mmol) and 4 Å molecular sieves (2.0 g) in THF (60 mL) was stirred for 30 min followed by the addition of CF3SiMe3 (5.8 g, 40 mmol) at −30° C. The mixture was kept overnight at room temperature, additional TBAF (20 g, 63 mmol) was added. After stirred additional 1 hour, the reaction was quenched by brine (40 mL) and extracted with ethyl acetate (3×50 mL). The organic layers combined, washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 5%-25% ethyl acetate in petroleum ether to afford 110 as a light yellow syrup (1.7 g, 49%). (ES, m/z): [M+H]+ 497.7; 1H NMR (300 MHz, CDCl3) δ 7.31-7.40 (m, 10H), 6.29 (d, J=6.6 Hz, 1H), 4.57-4.78 (m, 4H), 4.30-4.43 (m, 2H), 3.80-4.17 (m, 4H), 3.01 (s, 6H).

Provenance & Evidence