반응 #989184

반응 방정식

HCl

2-Bromo-6-methylpyridine

trimethylsilylacetylene

NaOH

→

2-Ethynyl-6-methyl-pyridine

용매

Et3N

MeOH

반응 조건

후처리

1. 1
   기타The solvent is removed in vacuo
2. 2
   workup.ADDITIONthe residue diluted in EtOAc (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 hours at room temp
8. 8
   추출extracted with dichloromethane
9. 9
   기타The solvent is removed in vacuo
10. 10
    기타to afford 1.16 g (24%) as a light yellow oil

실험 절차

2-Bromo-6-methylpyridine (0.5 g, 2.9 mmol) and trimethylsilylacetylene (0.29 g, 2.9 mmol) in Et3N (15 mL) is purged with argon. Then CuI (11 mg, 0.06 mmol) and (PPh3)2PdCl2 (42 mg, 0.06 mmol) are added and the reaction stirred under argon at room temp for 2 hours. The solvent is removed in vacuo and the residue diluted in EtOAc (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 MeOH (50 mL) and treated with a 1 N NaOH solution (10 mL) and stirred for 3 hours at room temp. The aqueous is then acidified to pH=4 with 1 N HCl and extracted with dichloromethane. The solvent is removed in vacuo to afford 1.16 g (24%) as a light yellow oil used as is in following reactions. 1H NMR (CDCl3) δ: 7.54 (t, 1H), 7.29 (d, 1H), 7.12 (d, 1H), 3.12 (s, 1H), 2.55 (s, 1H). MS ES+ m/e 118.1 (M+1).

출처