Salicylaldehyde → Benzofuran-2-yl-(5-methyl-3-phenyl-isoxazol-4-yl)-methanone

HRID 132599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132599
Br[CH2:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=[O:4].[CH:17](=O)[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[CH:17]=[C:2]1[C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=[O:4]

Komponenten

5

Edukt 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 27355314-(Bromoacetyl)-5-methyl-3-phenylisoxazole

Produkt 1

HCID 69106966Benzofuran-2-yl-(5-methyl-3-phenyl-isoxazol-4-yl)-methanoneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-(bromoacetyl)-5-methyl-3-phenylisoxazole (commercially available) (140 mg, 0.5 mmol) in DMF (0.5 mL) was added salicylaldehyde (61 mg, 53 μL, 0.5 mmol) followed by potassium carbonate (138 mg, 1.0 mmol) and the resulting mixture stirred vigorously at room temperature for 2 h. The mixture was then poured onto ice-water, and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over Na2SO4 and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 1:1) afforded the title compound (131 mg, 86%) as a white solid. MS m/e: 304.0 [M+H]+.

Aufarbeitung

  1. additionThe mixture was then poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4379a3071e2943828002ed1f4588bafc
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388025B2

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