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ChemicalBook CAS DataBase List 3-Butyn-1-ol, 4-(2-pyridinyl)- (9CI)
395652-44-5

3-Butyn-1-ol, 4-(2-pyridinyl)- (9CI) synthesis

4synthesis methods
2-Iodopyridine

5029-67-4

3-Butyn-1-ol

927-74-2

3-Butyn-1-ol, 4-(2-pyridinyl)- (9CI)

395652-44-5

In a sealed tube, 2-iodopyridine (1 mmol, 1 eq.), K3PO4 (2 mmol, 2 eq.) and palladium catalyst (2 mol%) were suspended in a solvent mixture of isopropanol (3 mL) and water (3 mL). Subsequently, 3-butyn-1-ol (1.2 mmol, 1.2 eq.) was added and the reaction mixture was stirred at 80 °C for 20 hours. After completion of the reaction, it was cooled to room temperature, diluted by adding ethyl acetate (20 mL) and water (20 mL), and then filtered. The aqueous phase was extracted twice with ethyl acetate (2 x 20 mL). The organic phases were combined, washed with saturated saline (60 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography.

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Yield:395652-44-5 90%

Reaction Conditions:

with copper(l) iodide;potassium carbonate;bis(η3-allyl-μ-chloropalladium(II));(1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane in N,N-dimethyl-formamide at 100; for 20 h;

References:

Feuerstein, Marie;Doucet, Henri;Santelli, Maurice [Tetrahedron Letters,2005,vol. 46,# 10,p. 1717 - 1720]