반응 #157686

반응 방정식

Trifluoroacetic anhydride

ethyl 5-cyclopropylpyridine-2-carboxylate 1-oxide

water

→

ethyl 5-cyclopropyl-6-hydroxypyridine-2-carboxylate

수율 78.0%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   추출followed by extraction with ethyl acetate
2. 2
   세척The organic layer was washed with saturated aqueous sodium bicarbonate and brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   여과filtered
5. 5
   기타The solvent was then evaporated under reduced pressure
6. 6
   기타The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

실험 절차

Trifluoroacetic anhydride (23 mL) was added to a solution of ethyl 5-cyclopropylpyridine-2-carboxylate 1-oxide (15.4 g) in N,N-dimethylformamide (45 mL), and the mixture was stirred at 50° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give ethyl 5-cyclopropyl-6-hydroxypyridine-2-carboxylate (12.4 g, 78%) as a colorless powder.

출처