StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Trimethylsilane → {5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

HRID 1038605
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1038605
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:9]([O:18]CC2C=CC(OC)=CC=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2].C[SiH](C)C.FC(F)(F)C([O-])=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si:14]([CH3:15])([CH3:17])[CH3:16])[C:9]([OH:18])=[CH:8][N:7]=1)(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 70435TrimethylsilaneHCID 84468TrifluoroacetateHCID 516892Sodium BicarbonateHCID 57423117{5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

Produkt 1

HCID 57423119{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(5-((4-Methoxybenzyl)oxy)-4-((trimethylsilyl)ethynyl)pyridin-2-yl)methyl acetate (5.38 g, 11.1 mmol) which is a crude product obtained in a-5) was dissolved in dichloromethane (55 mL), added trimethylsilane (1.9 mL, 35.1 mmol) and trifluoroacetate (5.5 mL) at room temperature, and the mixture was stirred overnight. The reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions (pH=8 was confirmed). The reaction solution was filtered through a pad of celite. The obtained filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (1.54 g (yield 53%)) was obtained as a yellow oil.

Aufarbeitung

  1. customobtained in a-5)
  2. filtrationThe reaction solution was filtered through a pad of celite
  3. extractionThe obtained filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e0fc05b143dc4d9b9ee0970151055544
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08551985B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion