Реакция #11776

Уравнение реакции

water

2,5-Dichloro-nicotinoyl chloride

tributyl-stannane

→

title compound

Выход 34.4%

2,5-Dichloro-pyridine-3-carbaldehyde

Выход 34.4%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature for 4 hours
2. 2
   Экстракцияthe product was extracted with ethylacetate
3. 3
   Сушкаthe combined organics were dried over magnesium sulfate
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеSilica gel chromatography (10% ethyl acetate/hexanes) followed by recrystallization from hexanes/ethylacetate

Методика

To a solution of 2,5-Dichloro-nicotinoyl chloride (15 g, 0.071 mol) in tetrahydrofuran was added tributyl-stannane (24.9 g, 0.086 mol) portionwise over 45 minutes. The resulting mixture was stirred at ambient temperature for 50 minutes, and then treated with tetrakis(triphenylphosphine)palladium(0) (0.82 g, 0.00071 mol). The reaction mixture was stirred at ambient temperature for 4 hours, poured into water; the product was extracted with ethylacetate, the combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (10% ethyl acetate/hexanes) followed by recrystallization from hexanes/ethylacetate gave the title compound (4.3 g).

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