(furan-2-ylethynyl)triMethylsilane synthesis
- Product Name:(furan-2-ylethynyl)triMethylsilane
- CAS Number:40231-01-4
- Molecular formula:C9H12OSi
- Molecular Weight:164.28
Yield:40231-01-4 85%
Reaction Conditions:
with triethylamine;bis-triphenylphosphine-palladium(II) chloride;copper(l) iodide at 20; for 16 h;Inert atmosphere;Darkness;
Steps:
7
2-(Trimemylsilylethynyl)furan (7) :To a stirring solution of 6 (30% w/w, 79g, 407mmol) in 60OmL of triethylamine under nitrogen was added trimethylsilylacetylene (44g, 448mmol),dichlorobis(triphenylphosphine)palladium(II) (1Og, 14mmol), and copper (I) iodide (5.1g, 27mmol). The reaction mixture was allowed to stir at room temperature in the absence of light for 16 h. The thick reaction mixture was diluted with 100 mL of diethyl ether and passed through a pad of Celite 521. The pad was washed with 2 X 100 mL of diethyl ether and the combined filtrates were concentrated in vacuo at 50 torr. The residue was purified by flash chromatography on silica gel (hexanes) to give TMS-protected ethynylfuran 7 (56.9g, 85%) as a yellow oil:1H NMR (400 MHz, CDCI3): 0.22-0.28 (br(s), 9H), 6.37 (t, IH), 6.61 (d, IH), 7.36 (d, IH).
References:
WO2011/6061,2011,A1 Location in patent:Page/Page column 47
