3-Pyridinecarboxaldehyde → Pyridin-3-yl(thiophen-2-yl)methanol

HRID 52182

Reaktionsgleichung

Reaktionsgleichung von HRID 52182
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[Li].CO.C(Cl)(Cl)Cl>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([OH:8])[C:10]2[S:9][CH:13]=[CH:12][CH:11]=2)[CH:2]=1

Komponenten

5

Edukt 3

HCID 103713-PyridinecarboxaldehydeHCID 21584188Chloroform methanolHCID 178418439HCID 178418439, Verbindung

Produkt 1

HCID 650499Pyridin-3-yl(thiophen-2-yl)methanolAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 3-pyridinecarboxaldehyde (5.0 mL, 53 mmol) in THF at -78° C. was added 2-thienyllithium (1.0M in THF. 64 mL, 64 mmol) and the reaction mixture was stirred for 2 hours at -78° C. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with ether. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (5%, then 10% methanol/CHCl3) gave 2-(3-pyridylhydroxymethyl)thiophene (6.30 g, 62% yield).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with ether
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-821002a002e645fc8b3d520076f6a82a
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616596

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