4-Pentyn-1-ol → HCID 18679547, Verbindung

Temperatur

60 °C

To 8.4 g (20 mmol) Trifluoro-methanesulfonic acid 1-(4-bromo-phenyl)-1H-indol-5-yl ester in 30 ml piperidine were added 2.08 g (24 mmol) LiBr, 580 mg (0.05 eq) [1,2-Bis(diphenylphosphino)ethane]dichloropalladium(II) and 2.8 ml (30 mmol) 4-pentyn-1-ol. The mixture was stirred at 60° C. for 3 h, further 0.5 ml (5.4 mmol) 4-pentynol were added and stirred at 70° C. for 1 h. The reaction mixture was concentrated and dissolved in ether and water. 2M HCl was added and the inorganic phase was extracted with ether. The combined organic phases were washed with water and concentrated. The residue was dissolved in 50 ml EtOH and treated with 5 ml conc. NaOH at 50° C. for 30 min. The solution was concentrated and dissolved in water and ether. The organic phase was washed with water, dried over Na2SO4 and concentrated. Column chromatography with CH2Cl2 yielded 2.15 g (30%) 5-[1-(4-Bromo-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol as colorless viscous oil, MS: 353 (M, 1Br).

1. stirringstirred at 70° C. for 1 h
2. concentrationThe reaction mixture was concentrated
3. dissolutiondissolved in ether
4. addition2M HCl was added
5. extractionthe inorganic phase was extracted with ether
6. washThe combined organic phases were washed with water
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in 50 ml EtOH
9. additiontreated with 5 ml conc. NaOH at 50° C. for 30 min
10. concentrationThe solution was concentrated
11. dissolutiondissolved in water
12. washThe organic phase was washed with water
13. dry with materialdried over Na2SO4
14. concentrationconcentrated

ORD-Eintrag

ord-530ff9a2003e41618dd9b40dd8c2c4fa

Quelldatensatz

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06503907B2