Triethylsilane → Octanal, pentadecafluoro-

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A sample of triethylsilane (4.24 g, 36.5 mmol) was cooled to 0° C. and treated with 10% Pd/C (0.35 g). After the exotherm subsided, perfluorooctanoyl chloride (15.8 g, 36.5 mmol) was added dropwise, controlling the temperature below ca. 6°-8° C. The mixture was stirred for 1.0 hr at 0° C. Another 0.59 g triethylsilane was added, and the mixture was stirred for 1.5 hr. An additional 0.13 g of triethylsilane was added. After 1.0 hr, vacuum transfer gave 16.4 g of liquid which was cooled at -250°C. for several hours. The top liquid layer was removed from the solid to provide ca. 10.5 g of the titled product. 19F NMR: -81.3 (t of t's, J=9.8, 2.3), -121.8 (m), -122.3 (m), -123.0 (m), 123.7 (m), -125.4 (t of m's, with JFCCH =3 Hz ), -126.5 (m).

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