Reacción #2355151

Ecuación de reacción

water

4-hydroxybenzaldehyde

2-fluoropyridine

potassium carbonate

→

4-(pyrid-2-yloxy)benzaldehyde

Rendimiento 45.2%

Disolventes

dimethyl sulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to ambient temperature
2. 2
   OtroThe organic and aqueous layers were separated
3. 3
   Extracciónextracted with two 400 mL portions of diethyl ether
4. 4
   Lavadowashed with one 100 mL portion of aqueous 5% sodium hydroxide
5. 5
   Secadodried with sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   ConcentraciónThe filtrate was concentrated under reduced pressure
8. 8
   Otroto yield a residue, which
9. 9
   LavadoElution
10. 10
    Concentraciónconcentrated under reduced pressure

Procedimiento

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.

Fuente