3-Pyridinecarboxaldehyde → Phenyl(pyridin-3-yl)methanol

HRID 509197

Reaktionsgleichung

Reaktionsgleichung von HRID 509197
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1.C(OCC)(=O)C>[C:9]1([CH:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[OH:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 2

HCID 103713-PyridinecarboxaldehydeHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 234839Phenyl(pyridin-3-yl)methanolAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirring solution of nicotinaldehyde 75 (0.876 mL, 9.34 mmol) in THF (20 mL) at 0° C. was slowly added a 1M phenylmagnesium bromide solution (9.34 mL, 9.34 mmol) and the reaction mixture was allowed to warm to room temperature over 30 minutes. The crude solution was diluted with ethyl acetate and washed with water, dried over Na2SO4, filtered and concentrated to afford compound 76 (1.7 g, 98% yield) after purification by flash chromatography (50 to 100% EtOAc in hexanes).

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-465c2d8cab8547e098ef67278bd86b1c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096565B2

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