반응 #732498

반응 방정식

1-chloro-6-bromo-2-naphthol

→

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

수율 177.5%

용매

triethylamine

반응 조건

후처리

1. 1
   기타The compound (S7-3) was synthesized
2. 2
   기타disclosed in Synthesis
3. 3
   workup.ADDITIONwas added
4. 4
   온도by refluxing for 6 hours
5. 5
   온도The reaction mixture was cooled to room temperature
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   workup.ADDITIONEthyl acetate was added to the resulting residue
8. 8
   여과the mixture was filtered with Celite
9. 9
   세척The resulting solution was washed with 1N hydrochloric acid and water
10. 10
    건조dried over anhydrous magnesium sulfate
11. 11
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
12. 12
    기타the resulting residue was purified by silica gel column chromatography with a mixed solvent of heptane and ethyl acetate (3/1) as a developing solvent
13. 13
    기타dried under reduced pressure

실험 절차

The compound (S7-3) was synthesized according to the method disclosed in Synthesis, No. 9, 1439 (2004). 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 under a nitrogen atmosphere and stirred at room temperature, to which 35.8 g of 1-heptine (S7-2) was added, followed by refluxing for 6 hours. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the resulting residue, and the mixture was filtered with Celite. The resulting solution was washed with 1N hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography with a mixed solvent of heptane and ethyl acetate (3/1) as a developing solvent and dried under reduced pressure to provide 32.3 g of 1-chloro-6-(1-pentynyl)-2-naphthol (S7-3).

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