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Water → {5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

HRID 1038604
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1038604
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:10](OS(C(F)(F)F)(=O)=O)=[CH:11][C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39].O>C(#N)C.[Cu](I)I>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:10]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])=[CH:11][C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])=[N:13][CH:14]=2)=[CH:5][CH:4]=1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 57423118(5-((4-Methoxybenzyl)oxy)-4-(((trifluoromethyl)sulfonyl)oxy)pyridin-2-yl)methyl acetate

Produkt 1

HCID 57423117{5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetateAusbeute 504,6 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 83717Copper iodideKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

(5-[(4-Methoxybenzyl)oxy]-4-{[(trifluoromethyl)sulfonyl]oxy}pyridin-2-yl)methylacetate (1.2 g, 2.78 mmol) was dissolved in acetonitrile (9.3 mL), added copper iodide (53 mg, 278 μmol), ditriphenylphosphine palladium (II) dichloride (98 mg, 139 μmol), triethylamine (8.0 mL) and trimethylsilyl acetylene (819 mg, 8.34 mmol) under an argon atmosphere, and under ice-cold conditions, and the mixture was stirred at 45° C. overnight. This operation was conducted for 4 lots, and the following treatments were conducted as a whole. The reaction solution was added water, and 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. A crude product of the title compound (5.38 g) was obtained as a yellow oil.

Aufarbeitung

  1. filtrationfiltered through a pad of celite
  2. extractionThe obtained filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e1a69b817c5f419fb5c1b9d1e1a9dde6
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08551985B2

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