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

HRID 1974506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1974506
[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)prop-2-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-37ae93597e0b440f89003812c7da6dbf
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05283245

Notizen zur Reaktion

Wird geladen…