반응 #8310

반응 방정식

hydrochloric acid

2-bromo-6-methylpyridine

(trimethylsilyl)acetylene

sodium hydroxide

→

title compound

2-Ethynyl-6-methyl-pyridine

용매

triethylamine

methanol

반응 조건

후처리

1. 1
   기타The solvent is removed in vacuo
2. 2
   workup.ADDITIONthe residue is diluted in ethyl acetate (50 mL)
3. 3
   기타The organic is separated
4. 4
   세척washed with brine
5. 5
   기타The solvent is removed
6. 6
   기타to afford a dark oil
7. 7
   workup.STIRRINGstirred for 3 h at room temperature
8. 8
   추출extracted with ethyl acetate
9. 9
   기타The solvent is removed in vacuo
10. 10
    기타to afford a dark oil that
11. 11
    기타is purified by SiO2 column chromatography

실험 절차

A solution of 2-bromo-6-methylpyridine (0.5 g, 2.9 mmol) and (trimethylsilyl)acetylene (0.29 g, 2.9 mmol) in triethylamine (15 mL) is purged with argon. Copper(I) iodide (11 mg, 0.06 mmol) and (PPh3)2PdCl2 (42 mg, 0.06 mmol) are added and the reaction is stirred under argon at room temperature for 2 h. The solvent is removed in vacuo and the residue is diluted in ethyl acetate (50 mL) and water (50 mL). The organic is separated and washed with brine. The solvent is removed to afford a dark oil. This oil is diluted in methanol (50 mL) and treated with a 1 N sodium hydroxide solution (10 mL) and stirred for 3 h at room temperature. The aqueous is neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The solvent is removed in vacuo to afford a dark oil that is purified by SiO2 column chromatography to yield 1.16 g (24%) of the title compound as a light yellow oil.

출처