Reaktion #474615

Reaktionsgleichung

H2O

K2CO3

3-hydroxypyridine

methyl 4-fluorobenzoate

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title product

Ausbeute 32.3%

methyl 4-(pyridine-3-yloxy)benzoate

Ausbeute 32.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled down to ambient temperature
2. 2
   ExtraktionThe resulting solution was extracted 3 times with ca. 150 mL of EtOAc (during the extraction small volumes of MeOH, Et2O and brine
3. 3
   workup.ADDITIONwere added
4. 4
   Sonstigethe separation)
5. 5
   WaschenCombined EtOAc layers were washed twice with sat. NaHCO3, twice with brine
6. 6
   Trocknendried over anhydrous Na2SO4
7. 7
   SonstigeSolvent was removed in vacuo
8. 8
   Sonstigeto give dark-red oil, which
9. 9
   Sonstigewas purified by silica gel chromatography
10. 10
    workup.ADDITION1:1 mixture of EtOAc/Hexane as eluent

Vorschrift

3-hydroxypyridine (6.17 g, 64.87 mmol) was dissolved in 100 mL of anhydrous DMF under argon atmosphere. Solid K2CO3 (8.96 g, 64.87 mmol) was added, followed by neat methyl 4-fluorobenzoate (10.0 g, 64.87 mmol). The reaction mixture was heated at 135° C. for 10 hrs. The absence of the starting material was confirmed by LC/MS. The reaction mixture was cooled down to ambient temperature and poured into ca. 500 mL of H2O. The resulting solution was extracted 3 times with ca. 150 mL of EtOAc (during the extraction small volumes of MeOH, Et2O and brine were added to facilitate the separation). Combined EtOAc layers were washed twice with sat. NaHCO3, twice with brine and dried over anhydrous Na2SO4. Solvent was removed in vacuo to give dark-red oil, which was purified by silica gel chromatography using 1:1 mixture of EtOAc/Hexane as eluent to give the title product (4.8 g, 32.3% yield) as yellow solid.

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