Реакция #7250

Уравнение реакции

3-cyano-2-picoline

water

selenium(IV) oxide

→

title compound

Выход 10.0%

3-cyano-2-pyridinecarboxaldehyde

Выход 10.0%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   Температураat reflux overnight
2. 2
   КонцентрированиеThe reaction mixture was concentrated under reduced pressure
3. 3
   Другоеpurified by column chromatography on silica gel (Hexanes/ether, 3:1

Методика

To a solution of 3-cyano-2-picoline (166 mg, 1.41 mmol) in dioxane (3 mL) was added water (0.2 mL) and selenium(IV) oxide (228 mg, 2.05 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1 then 1:1) to afford the title compound (18 mg, 10%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.69 (dd, 1H, J=9, 6 Hz), 8.20 (d, 1H, J=9 Hz), 9.00 (d, 1H, J=3 Hz), 10.13 (s, 1H).

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