Dimethyl Sulfoxide → Methyl 4'-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylate

HRID 1845267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845267
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:26]1[S:27][CH:28]=[CH:29][N:30]=1.CS(C)=O>CCOC(C)=O>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:7]=[C:2]([O:1][C:26]3[S:27][CH:28]=[CH:29][N:30]=3)[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=2)=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Produkt 1

HCID 58187983Methyl 4'-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (100 mg, 0.41 mmol), potassium carbonate (114 mg, 0.83 mmol), 2-bromothiazole (0.38 mL, 4.2 mmol), and dimethyl sulfoxide (2.5 mL) was stirred at 135° C. overnight. After cooling, the mixture was diluted with EtOAc and washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, and concentrated. The residue was purified by flash chromatography (0-20% EtOAc/hexane) to afford the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (0-20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ac8b1129f3c34aacb66939bd96334b84
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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