反応 #40268

反応方程式

1-chloro-6-bromo-2-naphthol

1-heptyne

→

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

収率 88.7%

溶媒

triethylamine

反応条件

後処理

1. 1
   その他The synthesis of (S7-3)
2. 2
   その他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
   その他to remove the solvent
7. 7
   workup.ADDITIONthe residue was added with ethyl acetate
8. 8
   ろ過filtered by celite
9. 9
   洗浄The resulting solution was washed with 1N HCl(aq) and water
10. 10
    乾燥dried over anhydrous magnesium sulfate
11. 11
    その他The solvent was removed by distillation under a reduced pressure
12. 12
    その他The residue was purified by silica gel column chromatography
13. 13
    その他dried under a reduced pressure

実験手順

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).

出典