Réaction #40268

Équation de réaction

1-chloro-6-bromo-2-naphthol

1-heptyne

→

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

Rendement 88.7%

Solvants

triethylamine

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source