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

HRID 1720444

Reaktionsgleichung

Reaktionsgleichung von HRID 1720444
[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-8f9a716072bd4c0bb8c2d6b1c9629c25
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506261

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