Trimethylsilylacetylene → HCID 17981367, compound

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (0.52 g, 0.45 mmol) was added to a degassed suspension of trimethylsilyl acetylene (3.00 mL, 2.09 g, 21.2 mmol), 4-(2-ethylhexyloxy)iodobenzene (2) (4.27 g, 12.9 mmol) and copper (I) iodide (294 mg, 1.54 mmol) in tetrahydrofuran (20 mL) and triethylamine (30 mL). The mixture was stirred under argon at room temperature for 64.5 h. The solution was filtered through a short plug of silica with dichloromethane as eluent and the solvent removed. The residue was purified by column chromatography over silica with light petroleum as eluent to leave [4-(2-ethylhexyloxy)phenylethynyl]trimethylsilane (3) (2.93 mg, 75%) as a clear, colourless oil. (Found: C, 75.35; H, 9.85. C19H30OSi requires C, 75.43; H, 10.0%); νmax(film)/cm−1 2156 (C≡C); δH(400 MHz, CDCl3) 0.25 (9 H, s, SiMe3), 0.92 (6 H, m, CH3), 1.30-1.51 (8 H, m, CHCH2CH2CH2CH3 and CHCH2CH3) 1.72 (1 H, m, OCH2CH), 3.84 (2 H, d, J 5, OCH2CH) and 6.82 and 7.40 (4 H, AA′BB′, phenyl H); δc(100.6 MHz, CDCl3) 0.1, 11.1, 14.1, 23.0, 23.8, 29.0, 30.4, 39.3, 70.5, 92.2, 105.3, 114.3, 114.8, 133.4 and 159.6.

Provenance & Evidence