(Trifluoromethyl)trimethylsilane → HCID 86701119, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of TBAF (3.7 g, 14 mmol) and 4 Å molecule sieves in THF (200 mL) was stirred for 30 min at 0° C. followed by the addition of a solution of 118 (15 g, 35 mmol) and TMS-CF3 (20 g, 141 mmol) in THF (80 mL). After stirring for additional 12 hours at 25° C., additional TBAF (14 g, 54 mmol) was added, and the mixture was stirred for 1 hour. The reaction was quenched by brine (200 mL), extracted with ethyl acetate (3×150 mL), the organic layers combined, washed with brine (3×100 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 119 (12 g, 69%) as a yellow oil; (ES, m/z) [M+H]+ 497.1. 1H NMR (300 MHz, CDCl3) δ 6.12-6.18 (m, 1H), 5.86-6.00 (m, 2H), 5.19-5.37 (m, 4H), 4.02-4.45 (m, 6H), 3.92-3.96 (m, 1H), 3.62-3.64 (m, 1H), 3.25 (d, J=3.6 Hz, 3H), 1.54-1.56 (m, 9H), 1.27-1.38 (m, 3H).

Provenance & Evidence