Potassium Carbonate → Methyl 3-[3,5-Diisopropyl-4-(1-phenyltetrazol-5-yloxy)benzoyl]propionate

HRID 976351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 976351
[OH:1][C:2]1[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:5]([C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])=[CH:4][C:3]=1[CH:19]([CH3:21])[CH3:20].Cl[C:23]1[N:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:26]=[N:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:16]([C:15]1[CH:14]=[C:5]([CH:4]=[C:3]([CH:19]([CH3:21])[CH3:20])[C:2]=1[O:1][C:23]1[N:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:26]=[N:25][N:24]=1)[C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:17])[CH3:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 19967177Methyl 4-(4-hydroxy-3,5-diisopropylphenyl)-4-oxobutanoate

Produkt 1

HCID 19967146Methyl 3-[3,5-Diisopropyl-4-(1-phenyltetrazol-5-yloxy)benzoyl]propionateAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

11 g of Methyl 3-(4-hydroxy-3,5-diisopropylbenzoyl]propionate was dissolved in 200 ml of N,N-dimethylformamide, followed by the addition of 8.15 g of 5-chloro-1-phenyl-1H-tetrazol and 10.4 g of potassium carbonate. The obtained mixture was stirred for 1 hour under heating, cooled to room temperature by allowing to stand and poured onto ice-water. The resultant mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The obtained residue was purified by silica gel chromatography (developer: 20% ethyl acetate/n-hexane) to give 14.1 g of the title compound as a white solid.

Aufarbeitung

  1. temperatureunder heating
  2. additionpoured onto ice-water
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with a saturated aqueous solution of common salt
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe obtained residue was purified by silica gel chromatography (developer: 20% ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4bcc7cdbe3e64846bedb6f0ba6865d75
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05612356

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