Potassium Carbonate → 3-(1,3-oxazol-5-yl)benzoic Acid

HRID 2250552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250552
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=[O:2].C1(C)C=CC(S([CH2:21][N+:22]#[C-:23])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[O:2]1[C:1]([C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=2)[C:6]([OH:8])=[O:7])=[CH:23][N:22]=[CH:21]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 120773-CarboxybenzaldehydeHCID 161915Tosylmethyl isocyanide

Produkt 1

HCID 71278133-(1,3-oxazol-5-yl)benzoic AcidAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 3-formylbenzoic acid (500 mg) and p-toluenesulfonylmethyl isocyanide (715 mg) in methanol (20 mL) was added potassium carbonate (1.38 g) and the mixture was heated under reflux for 2 hours. After evaporation of solvent, the residue was partitioned between ethyl acetate and water. The aqueous layer was separated and acidified with 1N hydrochloric acid. The resulting precipitates were collected and washed with water, methanol and ether to give 3-(1,3-oxazol-5-yl)benzoic acid as a colorless amorphous powder (484 mg).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of solvent
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe aqueous layer was separated
  6. customThe resulting precipitates
  7. customwere collected
  8. washwashed with water, methanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-1e475ecbef0744a8998861b294b6ed02
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07317009B2

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