Реакция #2487394

Уравнение реакции

lithium aluminum hydride

2-hydroxynicotinic acid

→

3-hydroxymethyl-2-pyridone

Выход 32.4%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеreturned to room temperature
2. 2
   Температураbefore being refluxed for 8 h
3. 3
   ТемператураThe reaction was cooled to room temperature
4. 4
   Другоеwas quenched with 1.6 mL of water, 1.6 mL of 15% NaOH
5. 5
   ДругоеThe solvent was removed in vacuo
6. 6
   ФильтрацияThe solution was filtered through celite
7. 7
   Другоеthe solvent removed in vacuo

Методика

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.

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