Uses
2-Ethynylpyridine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.
Synthesis
The general procedure for the synthesis of 2-ethynylpyridine from 2-pyridynyltrimethylsilane was as follows: 2-((trimethylmethylsilyl)ethynyl)pyridine (175 mg, 1.0 mmol) was dissolved in a mixed solvent of methanol/dichloromethane (2 mL/1 mL). The reaction system was cooled to 0 °C and potassium hydroxide (112 mg, 2.0 mmol) was subsequently added. After stirring the reaction mixture for 0.5 h at 0 °C, the reaction was quenched with deionized water. The reaction mixture was extracted with dichloromethane (2 x 3 mL) and the organic phases were combined. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the target product 2-ethynylpyridine (80 mg, 80% yield).
References
[1] Angewandte Chemie - International Edition, 2015, vol. 54, # 27, p. 7949 - 7953
[2] Angew. Chem., 2015, vol. 127, # 27, p. 8060 - 8064,5
[3] Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 716 - 727
[4] Dalton Transactions, 2016, vol. 45, # 25, p. 10209 - 10221
[5] Phosphorus, Sulfur and Silicon and Related Elements, 2002, vol. 177, # 5, p. 1041 - 1045
