반응 #2355151

반응 방정식

water

4-hydroxybenzaldehyde

2-fluoropyridine

potassium carbonate

→

4-(pyrid-2-yloxy)benzaldehyde

수율 45.2%

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to ambient temperature
2. 2
   기타The organic and aqueous layers were separated
3. 3
   추출extracted with two 400 mL portions of diethyl ether
4. 4
   세척washed with one 100 mL portion of aqueous 5% sodium hydroxide
5. 5
   건조dried with sodium sulfate
6. 6
   여과filtered
7. 7
   농축The filtrate was concentrated under reduced pressure
8. 8
   기타to yield a residue, which
9. 9
   세척Elution
10. 10
    농축concentrated under reduced pressure

실험 절차

A stirred mixture of 36.7 grams (0.30 mole) of 4-hydroxybenzaldehyde, 12.9 mL (0.15 mole) of 2-fluoropyridine, and 41.0 grams (0.30 mole) of potassium carbonate, and 1.05 grams of 1,4,7,10,13,16-hexaoxacyclooctadecane in 200 mL of dimethyl sulfoxide was heated at 120° C. for four days. The reaction mixture was cooled to ambient temperature, and 500 mL of water was added. The organic and aqueous layers were separated. The aqueous layer was basified with aqueous 10% sodium hydroxide and extracted with two 400 mL portions of diethyl ether. The ether extracts were combined and washed with one 100 mL portion of aqueous 5% sodium hydroxide, followed by one 100 mL portion of aqueous 10% lithium chloride. The organic layer and extracts were combined, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to yield a residue, which was subjected to column chromatography on silica gel. Elution was accomplished with 15-20% acetone in petroleum ether mixtures. The product-containing fractions were combined and concentrated under reduced pressure, yielding 13.5 grams of 4-(pyrid-2-yloxy)benzaldehyde. The NMR spectrum was consistent with the proposed structure.

출처