Potassium Carbonate → 2-[1-[3-(3-(3-Pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazole

HRID 1534387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534387
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)([O:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH2:33]Br)[CH:26]=1>CC(C)=O>[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH2:33][O:1][C:2]2[CH:3]=[C:4]([C:8]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)([O:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=2)[CH:26]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 156373793-[1-Methoxy-1-(1,3-thiazol-2-yl)propyl]phenolHCID 167329213-(3-Bromoprop-1-ynyl)pyridine hydrobromide

Produkt 1

HCID 191016422-[1-[3-(3-(3-Pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazoleAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-[1-(3-hydroxyphenyl)-1-methoxypropyl]thiazole (0.25 g), potassium carbonate (0.28 g), 3-(3-pyridyl)prop2-yn-1-yl bromide hydrobromide (0.28 g) and acetone (5 ml) was stirred and heated to reflux for 17 hours. The mixture was cooled to ambient temperature, filtered and the filtrate was evaporated. The residue was purified by column chromatography eluting with hexane/ethyl acetate (1:1 v/v) to give 2-[1-[3-(3-(3-pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazole as an oil (0.217 g, 59%).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 17 hours
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with hexane/ethyl acetate (1:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-83bb1010f6ee4e92a6577f3c0fba8d93
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05089495

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