Potassium Carbonate → 4-(4-Methyl-oxazol-5-yl)-benzoic acid methyl ester

HRID 68760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68760
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][CH:5]=1.[N+:13]([CH:15](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:16])#[C-:14].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:14]=[N:13][C:15]=2[CH3:16])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 15294Methyl 4-FormylbenzoateHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Produkt 1

HCID 682895774-(4-Methyl-oxazol-5-yl)-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-formyl-benzoic acid methyl ester (2.50 g), 1-(1-isocyano-ethanesulfonyl)-4-methyl-benzene (3.19 g), and potassium carbonate (2.76 g) in methanol (50 mL) is heated to reflux for 2 h. After cooling to room temperature, the mixture is poured onto water and extracted with dichloromethane. The organic phase is washed with water, dried over Na2SO4 and concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 40:1) to afford the title compound. LC (method 6): tR=2.68 min; Mass spectrum (ESI+): m/z=218 [M+H]+.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for 2 h
  3. additionthe mixture is poured onto water
  4. extractionextracted with dichloromethane
  5. washThe organic phase is washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on silica gel (dichloromethane/methanol 40:1)

Quellen und Nachweise

ORD-Eintrag
ord-7479719406c0480abf24392f099b2eff
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822471B2

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