An efficient synthesis of α-(trimethylsilyl)allenyl ketones

References

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• Spectral data for 3 showed IR: 2070s, 1625m cm−1; 1H NMR: 4.45,4.42 (AB pattern, J = 9.2 Hz, 2H), 2.01 (s, 3H), 0.23 (s, 9H). These parallel values previously reported (ref 3b) for similar (air-unstable) [3]cumulenyloxysilanes
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• As determined from IR and 1HNMR analysis of the crude reaction product
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• Comparative yields were calculated starting with the 3-trimethylsiloxy-1-alkyne or from ethynylmagnesium bromide and acetyltrimethylsilane as employed in ref. 1
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• No product was obtained when THF was used as solvent
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• Prepared by refluxing powdered ZnCl2 in SOCI2 18h, evacuation at 80°C (1 mm), dissolution in anhydrous ether and filtration through a 0.2 μm PTFE syringe filter
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