반응 #11776

반응 방정식

water

2,5-Dichloro-nicotinoyl chloride

tributyl-stannane

→

title compound

수율 34.4%

2,5-Dichloro-pyridine-3-carbaldehyde

수율 34.4%

용매

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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).

출처