Potassium Carbonate → Methyl 2-(5-Oxazolyl)benzoate

HRID 240399

Reaktionsgleichung

Reaktionsgleichung von HRID 240399
[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[O:2].S([CH2:23][N+:24]#[C-:25])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[O:2]1[C:1]([C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[C:5]([O:7][CH3:8])=[O:6])=[CH:25][N:24]=[CH:23]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 243003Methyl 2-formylbenzoate

Produkt 1

HCID 73553912Methyl 2-(5-Oxazolyl)benzoateAusbeute 21,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-formylbenzoate (15 g) and tosylmethyl isocyanide (18 g) in methanol (250 mL) was added potassium carbonate (15 g), and the mixture was heated under reflux for 16 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (4.0 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washthe mixture was washed with water and saturated brine
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-12e6e531a8bc426682e21d1614a7f5d8
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648079B2

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