تفاعل #11776

معادلة التفاعل

water

2,5-Dichloro-nicotinoyl chloride

tributyl-stannane

→

title compound

المردود 34.4%

2,5-Dichloro-pyridine-3-carbaldehyde

المردود 34.4%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر