4-Cyanopyridine → 4-[(Trimethylsilyl)ethynyl]pyridine

Participants

Reaction Steps

The procedure was identical to Example 1, with the exception that 4-cyanopyridine (0.208 g; 2.00 mmol) was used as a substrate instead of benzonitrile and lithium trimethylacetylide (8.00 ml; 4.00 mmol; 0.5 M in THF) was used instead of the in situ derived lithium acetylide made from trimethylsilylacetylene and n-butyllithium. GC analysis of the organic phase of the hydrolyzed reaction sample after 20 h at 65° C. showed the presence of 1.12 mmol (56% yield) of 4-(trimethylsilylethynyl)pyridine and no remaining 3-cyanopyridine in the reaction mixture.

Provenance & Evidence