Methanol → HCID 22220954, Verbindung

HRID 1794445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1794445
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[CH:15][C:14]=3[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:28]O>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:17][N:16]=[CH:15][C:14]=3[CH2:18][CH2:19][C:20]([O:22][CH3:28])=[O:21])=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22221001HCID 22221001, Verbindung

Produkt 1

HCID 22220954HCID 22220954, VerbindungAusbeute 94 %

Versuchsvorschrift

A mixture of 3-[5-(4-phenylphenyl)-4-isoxazolyl]propionic acid (6.00 g), conc. sulfuric acid (0.1 ml) and methanol (100 ml) was refluxed for 4 hr. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[5-(4-phenylphenyl)-4-isoxazolyl]propionate (5.91 g, yield 94%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 103–104° C.

Aufarbeitung

  1. temperaturewas refluxed for 4 hr
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e507becbd4bc4be0bfb1a044bcb9eca3
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022725B2

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