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ChemicalBook CAS DataBase List 5-ETHYNYLPICOLINALDEHYDE

5-ETHYNYLPICOLINALDEHYDE synthesis

3synthesis methods
650606-63-6 Synthesis
5-((trimethylsilyl)ethynyl)picolinaldehyde

650606-63-6
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Yield:940911-03-5 95%

Reaction Conditions:

with methanol;potassium carbonate at 20; for 2 h;

Steps:

7.B

B. 5-[(Trimethylsilyl)ethynyl]pyridine-2-carbaldehyde; To a solution of 5-[(trimethylsilyl)ethynyl]pyridine-2-carbaldehyde (13 g, 64 mmol) in methanol was added potassium carbonate (0.9 g, 6.4 mmol), followed by stirring at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure (bath temperature below 40 0C). Ice cold water was added to the crude solid, the product precipitated, and the mixture was stirred for an additional 5 min at 0 0C. The precipitated solid was filtered and washed with water to provide 5- [(trimethylsilyl)ethynyl]pyridine-2-carbaldehyde (8 g, 95%) as light brown solid. LC-MS: [M+H]+ 132 1H NMR (400 MHz, CDCl3) δ: ppm 10.08 (s, IH), 8.86 (s, IH), 7.93 (m, 2H), 3.43 (s, IH).

References:

WO2010/100475,2010,A1 Location in patent:Page/Page column 55-56