Dimethylformamide → (5-Tert-butyl-2-methyl-phenylethynyl)trimethyl-silane

Participants

Reaction Steps

Following General Procedure D and using trifluoro-methanesulfonic acid 5-tert-butyl-2-methyl-phenyl ester (Intermediate 108, 0.28 g, 0.94 mmol), triethyl amine (3 mL), trimethylsilyl acetylene (1 mL, 7 mmol), N,N-dimethylformamide (6 mL) and dichlorobis(triphenylphosphine)palladium(II) (0.053 g, 0.076 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane as the eluent, the title compound (0.16 g, 69%) was obtained. 1H NMR (300 MHz, CDCl3): δ 7.44 (d, J=1.7 Hz, 1H), 7.22 (dd, J=8.2, 1.7 Hz, 1H), 7.10 (d, J=8.2 Hz, 1H), 2.39 (s, 3H), 1.28 (s, 9H), 0.26 (s, 9H).

Provenance & Evidence