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4-Pentyn-1-ol → 5-[1-(4-Trimethylsilanylethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol

HRID 1633663
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1633663
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18](OS(C(F)(F)F)(=O)=O)=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[CH:9][CH:8]=1)([CH3:4])[CH3:3].[CH2:30]([OH:35])[CH2:31][CH2:32][C:33]#[CH:34]>N1CCCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[CH3:3][Si:2]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:34]#[C:33][CH2:32][CH2:31][CH2:30][OH:35])=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[CH:11][CH:12]=1)([CH3:4])[CH3:1]
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Komponenten

6

Edukt 2

HCID 793464-Pentyn-1-olHCID 86585591Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl ester

Produkt 1

HCID 186794765-[1-(4-Trimethylsilanylethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-olAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 8082PiperidineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 1.62 g (3.7 mmol) Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl ester in 5 ml piperidine, 230 mg (0.2 mmol) tetrakis-(triphenylphosphine)-palladium and 40 mg (0.2 mmol) CuI were added. The solution was evaporated and purged with argon three times, before 0.56 ml (6 mmol) 4-pentyn-1-ol were added. The solution was stirred at 80° C. for 2 h. The solution was concentrated and the residue dissolved in 0.5M HCl and ether. The inorganic phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Purification on silica gel with CH2Cl2 yielded 980 mg (71%) 5-[1-(4-Trimethylsilanylethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol as orange viscous oil, MS: 371 (M).

Aufarbeitung

  1. customThe solution was evaporated
  2. additionwere added
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue dissolved in 0.5M HCl
  5. extractionThe inorganic phase was extracted with ether
  6. washthe organic phases were washed with water
  7. dry with materialdried over Na2SO4
  8. customPurification on silica gel with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-f7f57941906c4b52887534cd90ccc342
Quelldatensatz
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06503907B2

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