Potassium Iodide → HCID 69280462, Verbindung

HRID 1064881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064881
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([O:14][CH2:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].Cl[CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[O:23][C:24]=1[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([O:14][CH2:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[O:23][C:24]=2[CH3:25])=[CH:8][C:7]=1[CH3:13]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 219742584-(Chloromethyl)-5-methyl-2-(2-methylphenyl)-1,3-oxazoleHCID 68616579(S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester

Produkt 1

HCID 69280462HCID 69280462, VerbindungAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of (S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (80 mg, 0.34 mmol), 4-chloromethyl-5-methyl-2-o-tolyl-oxazole (82 mg, 0.37 mmol), cesium carbonate (120 mg, 0.37 mmol) and a trace of potassium iodide were suspended in acetone (8 ml). The suspension was heated under reflux for 5 h, the solvent evaporated under reduced pressure and the residue dissolved in 2 N HCl/ice water 1/1 and ethyl acetate. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed two times with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, cyclohexane/AcOEt) to give 100 mg (0.24 mmol, 70%) of the title compound as yellow oil.

Aufarbeitung

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 5 h
  3. customthe solvent evaporated under reduced pressure
  4. dissolutionthe residue dissolved in 2 N HCl/ice water 1/1
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted two times with ethyl acetate
  7. washThe combined organic layers were washed two times with brine
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe residue purified by column chromatography (silica gel, cyclohexane/AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-3dbcf44e59ee4ff99c88759e84e6073e
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969725B2

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