Tetrabutylammonium Fluoride → (6-Ethylpyridin-3-yl)methanol

HRID 1296004

Reaktionsgleichung

Reaktionsgleichung von HRID 1296004
C(C1([SiH2][C:12]([O:28]C(C2C=NC(CC)=CC=2)([SiH2]C2C=CC=CC=2)[SiH2]C2(C(C)(C)C)C=CC=CC2)([C:20]2[CH:21]=[N:22][C:23]([CH2:26][CH3:27])=[CH:24][CH:25]=2)[SiH2]C2C=CC=CC=2)C=CC=CC1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH2:26]([C:23]1[N:22]=[CH:21][C:20]([CH2:12][OH:28])=[CH:25][CH:24]=1)[CH3:27]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 137328928HCID 137328928, Verbindung

Produkt 1

HCID 22929790(6-Ethylpyridin-3-yl)methanolAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

After dissolving the 1-(tert-butyl)-1,1-diphenylsilyl [(6-ethyl-3-pyridyl)methyl]ether (7.81 g, 20.8 mmol) in tetrahydrofuran (80 ml), TBAF (31.2 ml, 31.2 mmol) was added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched with water and was extracted with ethyl acetate. After washing the extract with brine, it was dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (2.25 g) as a colorless oil. (78.8% yield)

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was quenched with water
  3. extractionwas extracted with ethyl acetate
  4. washAfter washing the
  5. extractionextract with brine, it
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-00a8ca9c29534c86bd412372dd42774b
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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