(Trifluoromethyl)trimethylsilane → HCID 69093936, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of TBAF (1.1, 4.2 mmol) and 4 Å molecular sieves (4 g) in THF (40 mL) was stirred for 30 minutes at 0° C., followed by addition of a mixture of 144 (4.6 g, 8.3 mmol) and CF3TMS (5.9 g, 42 mmol) in THF (40 mL). The mixture was stirred for 3 hours at room temperature, followed by addition of additional TBAF (6 g, 22 mmol). After 1 hour, the reaction was then quenched by addition of water (80 mL). A filtration was performed and the filtrate was extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (2×30 mL), dried over magnesium sulfate, and concentrated. The residue was purified by flash column chromatography with 6%-12% ethyl acetate in petroleum ether to afford the title compound as a brown syrup (3.5 g, 68%, two isomers, ratio is 1:1 determined by 1H NMR). (ES, m/z): [M+H]+ 623.0; 1H NMR (300 MHz, CDCl3): 7.37-7.23 (m, 10H), 6.13-6.07 (m, 1H), 5.76-5.74 (m, 1H), 5.05-4.92 (m, 2H), 4.74-4.67 (m, 2H), 4.47-4.25 (m, 7H), 3.93-3.88 (m, 1H), 1.50 (s, 9H), 1.28-1.23 (m, 3H).

Provenance & Evidence