반응 #40268

반응 방정식

1-chloro-6-bromo-2-naphthol

1-heptyne

→

1-chloro-6-(1-pentynyl)-2-naphthol

수율 88.7%

용매

triethylamine

반응 조건

후처리

1. 1
   기타The synthesis of (S7-3)
2. 2
   기타described in Synthesis
3. 3
   온도refluxed for 6 hours
4. 4
   온도The reaction solution was cooled to room temperature
5. 5
   workup.DISTILLATIONdistilled under a reduced pressure
6. 6
   기타to remove the solvent
7. 7
   workup.ADDITIONthe residue was added with ethyl acetate
8. 8
   여과filtered by celite
9. 9
   세척The resulting solution was washed with 1N HCl(aq) and water
10. 10
    건조dried over anhydrous magnesium sulfate
11. 11
    기타The solvent was removed by distillation under a reduced pressure
12. 12
    기타The residue was purified by silica gel column chromatography
13. 13
    기타dried under a reduced pressure

실험 절차

The synthesis of (S7-3) was carried out following the method described in Synthesis, No. 9, 1439 (2004). At first, 38.3 g of 1-chloro-6-bromo-2-naphthol (S1-2), 5.2 g of PdCl2(PPh3)2, 0.71 g of copper iodide and 400 ml of triethylamine were added to a reactor in nitrogen atmosphere, stirred at room temperature, added with 35.8 g of 1-heptyne (S7-2) and then refluxed for 6 hours. The reaction solution was cooled to room temperature and distilled under a reduced pressure to remove the solvent, and then the residue was added with ethyl acetate and filtered by celite. The resulting solution was washed with 1N HCl(aq) and water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under a reduced pressure. The residue was purified by silica gel column chromatography using heptane/ethyl acetate=3/1 as an eluting solvent and dried under a reduced pressure to obtain 32.3 g of 1-chloro-6-(1-pentynyl)-2-naphthol (S7-3).

출처