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Sodium Bicarbonate → 4-Ethylphenyl-3-hydroxypyridin-2-yl-methanol

HRID 2116498
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2116498
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[C:16]([O:17]COCC[Si](CC)(CC)CC)=[CH:15][CH:14]=[CH:13][N:12]=2)[OH:10])=[CH:5][CH:4]=1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[OH:10])=[CH:7][CH:8]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 69220512HCID 69220512, Verbindung

Produkt 1

HCID 231036174-Ethylphenyl-3-hydroxypyridin-2-yl-methanolAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 4-ethylphenyl-[3-[2-(triethylsilyl)ethoxymethoxy]]pyridin-2-yl-methanol (2.35 g, 6.54 mmol) in THF-water (25:1; 60 mL), p-toluenesulfonic acid monohydrate (2.8 g, 16.4 mmol) was added and stirred at room temperature for 20 hours and at 40° C. for 4 hours. After cooling the reaction mixture to room temperature, saturated sodium bicarbonate solution (100 mL) was added and the resulting mixture was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 4-ethylphenyl-3-hydroxypyridin-2-yl-methanol (0.62 g).

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. extractionthe resulting mixture was then extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-092eb62a49484917bc40e88e61630e6d
Quelldatensatz
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07439232B2

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