Water → (+/-)-1-(Benzofuran-6-yloxy)-4-pyridin-3-yl-butan-2-ol

HRID 1856688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1856688
Cl[CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[OH:13][C:14]1[CH:22]=[CH:21][C:17]2[CH:18]=[CH:19][O:20][C:16]=2[CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[O:20]1[C:16]2[CH:15]=[C:14]([O:13][CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)[CH:22]=[CH:21][C:17]=2[CH:18]=[CH:19]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1288446-HydroxybenzofuranHCID 22465338HCID 22465338, Verbindung

Produkt 1

HCID 22132417(+/-)-1-(Benzofuran-6-yloxy)-4-pyridin-3-yl-butan-2-olAusbeute 24,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

##STR16## (±)-α-(Chloromethyl)-3-pyridinepropanol (0.339 g, Example 2a)) was dissolved in anhydrous N,N-dimethylformamide (5 ml) and added to a suspension of 6-hydroxybenzofuran (0.245 g, Bull. Soc. Chim. Fr., 1973, 2355) and cesium carbonate (0.596 g) in anhydrous N,N-dimethylformamide (5 ml) which had been heated previously for one hour at 120° C. The mixture was then heated at 120° C. for 7 hours before being cooled to room temperature. The mixture was then poured into water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:ethanol (19:1) and recrystallised from ethyl acetate:hexane to give the title compound (0.129 g).

Aufarbeitung

  1. temperatureThe mixture was then heated at 120° C. for 7 hours
  2. temperaturebefore being cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography over silica eluting with dichloromethane:ethanol (19:1)
  9. customrecrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-af602329fe954273a4521369291998f5
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06143751

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