Cesium carbonate → 3-(2-Oxooxazolidin-3-yl)benzoic Acid Methyl Ester

HRID 1612441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1612441
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[O:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([N:20]2[CH2:21][CH2:22][O:18][C:19]2=[O:23])[CH:3]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 12070Methyl 3-bromobenzoateHCID 739492-OxazolidinoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Produkt 1

HCID 695897133-(2-Oxooxazolidin-3-yl)benzoic Acid Methyl EsterAusbeute 21,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Methyl 3-bromobenzoate (500 mg, 2.33 mmol), caesium carbonate (1.06 g, 3.26 mmol), oxazolidin-2-one (243 mg, 2.80 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (107 mg, 0.186 mmol) and tris(dibenzylideneacetone)dipalladium (0) (43 mg, 0.047 mmol) were refluxed under argon in dioxane (6 ml) for 18 h. After cooling, the mixture was filtered and evaporated in vacuo. Column chromatography on silica gel eluting with a gradient of 10–50% ethyl acetate in hexane gave the title compound (113 mg).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5fc2000416bf4e678773e8b3eb663a12
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992103B2

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