Reaction #40268

Reaction equation

1-chloro-6-bromo-2-naphthol

1-heptyne

→

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

Yield 88.7%

Solvents

triethylamine

Conditions

Workup

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

Procedure

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