Reaktion #2487394

Reaktionsgleichung

lithium aluminum hydride

2-hydroxynicotinic acid

→

3-hydroxymethyl-2-pyridone

Ausbeute 32.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereturned to room temperature
2. 2
   Temperaturbefore being refluxed for 8 h
3. 3
   TemperaturThe reaction was cooled to room temperature
4. 4
   Sonstigewas quenched with 1.6 mL of water, 1.6 mL of 15% NaOH
5. 5
   SonstigeThe solvent was removed in vacuo
6. 6
   FiltrationThe solution was filtered through celite
7. 7
   Sonstigethe solvent removed in vacuo

Vorschrift

In Example 1, 1.6063 g (42.33 mmol) of lithium aluminum hydride (LAH) was suspended in 100 mL of tetrahydrofuran (THF) in a 250 mL round bottom flask (RBF) under the presence of argon gas (99.999% purity) and was cooled to 0° C. in an ice bath. 5.0946 g (36.62 mmol) of 2-hydroxynicotinic acid was slowly added, and the solution returned to room temperature before being refluxed for 8 h. The reaction was cooled to room temperature and was quenched with 1.6 mL of water, 1.6 mL of 15% NaOH and an additional 4.8 mL of water. The solvent was removed in vacuo and the residue was taken up in 100 mL of refluxing ethanol. The solution was filtered through celite and the solvent removed in vacuo to produce 1.4848 g (32.40% yield) of 3-hydroxymethyl-2-pyridone. Characterization data of the product was consistent with literature.

Quelle