反应 #40268

反应方程式

1-chloro-6-bromo-2-naphthol

1-heptyne

→

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

收率 88.7%

溶剂

triethylamine

反应条件

后处理

1. 1
   其他The synthesis of (S7-3)
2. 2
   其他described in Synthesis
3. 3
   温度refluxed for 6 hours
4. 4
   温度The reaction solution was cooled to room temperature
5. 5
   workup.DISTILLATIONdistilled under a reduced pressure
6. 6
   其他to remove the solvent
7. 7
   workup.ADDITIONthe residue was added with ethyl acetate
8. 8
   过滤filtered by celite
9. 9
   洗涤The resulting solution was washed with 1N HCl(aq) and water
10. 10
    干燥dried over anhydrous magnesium sulfate
11. 11
    其他The solvent was removed by distillation under a reduced pressure
12. 12
    其他The residue was purified by silica gel column chromatography
13. 13
    其他dried under a reduced pressure

实验过程

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).

来源