Hydrochloric Acid → 1-(Benzo[b]furan-5-yl)-2-(pyridin-3-ylmethoxy)ethanol

HRID 976544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 976544
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.CC(C)([O-])C.[K+].[O:15]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21]([CH:24]3[CH2:26][O:25]3)[CH:22]=[CH:23][C:16]1=2.Cl>C(OCC)(=O)C.CS(C)=O>[O:15]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21]([CH:24]([OH:25])[CH2:26][O:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:22]=[CH:23][C:16]1=2

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 75103-PyridinemethanolHCID 23665647Potassium tert-butoxideHCID 451225992-(Benzo[b]furan-5-yl)oxirane

Produkt 1

HCID 544244681-(Benzo[b]furan-5-yl)-2-(pyridin-3-ylmethoxy)ethanolAusbeute 14,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1.6 g of 3-pyridinemethanol, 1.7 g of potassium tert-butoxide and 23 ml of dimethyl sulfoxide was heated to 80°πC. Thereto was added 2.4 g of 2-(benzo[b]furan-5-yl)oxirane. The resulting mixture was stirred at 85°-90° C. for 15 minutes. The reaciton mixture was added to a mixture of 50 ml of ice water and 50 ml of ethyl acetate. The resulting mixture was adjusted to pH 1 with 6N hydrochloric acid. The aqueous layer was separated and 30 ml of ethyl acetate was added thereto. The resulting mixture was adjusted to pH 9.5 with potassium carbonate. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/ethanol=50/1) to obtain 0.56 g of 1-(benzo[b]furan-5-yl)-2-(pyridin-3-ylmethoxy)ethanol (compound No. 339).

Aufarbeitung

  1. temperaturewas heated to 80°πC
  2. customThe aqueous layer was separated
  3. addition30 ml of ethyl acetate was added
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by column chromatography (eluant: chloroform/ethanol=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-146bf2a463e4414a978c0a58d6760537
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05612381

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