Benzyl 4-Hydroxybenzoate → Benzyl 4-(pyridin-3-yloxy)benzoate

HRID 1610600

Reaktionsgleichung

Reaktionsgleichung von HRID 1610600
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1>CN(C)C=O.[Cu]>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([O:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][CH:3]=2)[CH:26]=1

Komponenten

6

Edukt 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 122863-BromopyridineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 22262109Benzyl 4-(pyridin-3-yloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of benzyl 4-hydroxybenzoate (25.0 g, 110 mmol) in N,N-dimethylformamide (60 ml) was added potassium tert-butoxide (12.3 g, 110 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction solution was evaporated under reduced pressure, and 3-bromopyridine (25.0 g, 110 mmol), a copper powder (1.76 g, 27.2 mmol) and N,N-dimethylformamide (80 ml) were added. The mixture was stirred at 120° C. for 8 hrs. The reaction solution was filtered with celite and the filtrate was evaporated under reduced pressure. To the residue was added water (500 ml) and the mixture was extracted with ethyl acetate (500 ml). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-2:1) to give the objective substance (18.0 g, 54%, crude).

Aufarbeitung

  1. stirringThe mixture was stirred at 120° C. for 8 hrs
  2. filtrationThe reaction solution was filtered with celite
  3. customthe filtrate was evaporated under reduced pressure
  4. additionTo the residue was added water (500 ml)
  5. extractionthe mixture was extracted with ethyl acetate (500 ml)
  6. washThe extract was washed successively with water and saturated brine
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. customevaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-2:1)
  10. customto give the objective substance (18.0 g, 54%, crude)

Quellen und Nachweise

ORD-Eintrag
ord-3fadcb0b6113453aac7fa19ac40d1eab
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

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