Reaktion #40268

Reaktionsgleichung

1-chloro-6-bromo-2-naphthol

1-heptyne

→

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

Ausbeute 88.7%

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe synthesis of (S7-3)
2. 2
   Sonstigedescribed in Synthesis
3. 3
   Temperaturrefluxed for 6 hours
4. 4
   TemperaturThe reaction solution was cooled to room temperature
5. 5
   workup.DISTILLATIONdistilled under a reduced pressure
6. 6
   Sonstigeto remove the solvent
7. 7
   workup.ADDITIONthe residue was added with ethyl acetate
8. 8
   Filtrationfiltered by celite
9. 9
   WaschenThe resulting solution was washed with 1N HCl(aq) and water
10. 10
    Trocknendried over anhydrous magnesium sulfate
11. 11
    SonstigeThe solvent was removed by distillation under a reduced pressure
12. 12
    SonstigeThe residue was purified by silica gel column chromatography
13. 13
    Sonstigedried under a reduced pressure

Vorschrift

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).

Quelle