Hydroxyamine hydrochloride → Methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoate

HRID 1386593

Reaktionsgleichung

Reaktionsgleichung von HRID 1386593
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][CH:16]=2)=[O:14])=[CH:7][CH:6]=1)=[O:4].Cl.[NH2:29]O>CO.C(OCC)(=O)C>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[O:14][N:29]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[CH:12]=2)=[CH:16][CH:17]=1)[CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

5

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 11405985Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoate

Produkt 1

HCID 10737571Methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoateAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The solution of 1-(4-Methoxycarbonylphenyl)-3-(4-pentyloxyphenyl)propane-1,3-dione (1.00 g) and hydroxylamine hydrochloride (567 mg) in methanol (10 ml) was refluxed for 10 hours. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with water (50 ml×2), brine (50 ml). The organic layer was dried over magnesium sulfate and the solvents were removed under reduced pressure. The residue was triturated with acetonitrile (10 ml), collected by filtration, and dried under reduced pressure to give Methyl 4-[5-(4-pentyloxyphenyl)isoxazol-3-yl]benzoate (0.74 g).

Aufarbeitung

  1. washwashed with water (50 ml×2), brine (50 ml)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was triturated with acetonitrile (10 ml)
  5. filtrationcollected by filtration
  6. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c018834c36c34c2984f15ae90474f41d
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265536B1

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