Water → 4-[5-(4-n-Pentyloxyphenyl)isoxazol-3-yl]bromobenzene

HRID 1872408

Reaktionsgleichung

Reaktionsgleichung von HRID 1872408
[Cl-].[Br:2][C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[N:8][OH:9])=[CH:5][CH:4]=1.[CH2:12]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1)[CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.O>O1CCCC1>[CH2:12]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:9][N:8]=[C:7]([C:6]3[CH:10]=[CH:11][C:3]([Br:2])=[CH:4][CH:5]=3)[CH:25]=2)=[CH:20][CH:19]=1)[CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 27751191-Eth-1-ynyl-4-(pentyloxy)benzeneHCID 737528934-Bromobenzaldehyde oxime chloride

Produkt 1

HCID 211823474-[5-(4-n-Pentyloxyphenyl)isoxazol-3-yl]bromobenzeneAusbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 4-bromobenzaldehyde oxime chloride (647 mg) and 4-n-pentyloxy-phenylacetylene (650 mg) in tetrahydrofuran (7 ml) was added triethylamine (0.5 ml) in tetrahydrofuran (5 ml) dropwise at 40° C. The solution was stirred at 40° C. for 30 minutes, poured into water and extracted with ethyl acetate. The organic layer was washed with H2O, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with acetonitrile. The precipitate was collected by filtration and dried to give 4-[5-(4-n-pentyloxyphenyl)isoxazol-3-yl]bromobenzene (0.59 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was triturated with acetonitrile
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2dbae69dec4941e5ae28c523f32aeed9
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06107458

Verknüpfte Notizen

Wird geladen…