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Potassium Carbonate → Methyl 5-(2-(methoxymethyl)-4-methyloxazol-5-yl)-2,4-dimethylbenzoate

HRID 1487822
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1487822
Br[CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH3:16])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:4].Cl.[CH3:19][O:20][CH2:21][C:22](=[NH:24])[NH2:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:19][O:20][CH2:21][C:22]1[NH:23][C:3]([C:5]2[C:6]([CH3:16])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=2)[C:10]([O:12][CH3:13])=[O:11])=[C:2]([CH3:17])[N:24]=1.[CH3:19][O:20][CH2:21][C:22]1[O:4][C:3]([C:5]2[C:6]([CH3:16])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=2)[C:10]([O:12][CH3:13])=[O:11])=[C:2]([CH3:17])[N:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 135486022-Methoxyethanimidamide hydrochlorideHCID 90021223Methyl 5-(2-bromopropanoyl)-2,4-dimethylbenzoate2×

Produkt 2

HCID 90021632Methyl 5-(2-(methoxymethyl)-4-methyloxazol-5-yl)-2,4-dimethylbenzoateAusbeute 52 %HCID 178494667HCID 178494667, Verbindung
Ausbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Into a 100-mL round-bottom flask, was placed a mixture of methyl 5-(2-bromopropanoyl)-2,4-dimethylbenzoate (compound 1.6, 600 mg, 2.01 mmol), 2-methoxyethanimidamide hydrochloride (510 mg, 4.09 mmol), potassium carbonate (840 mg, 6.08 mmol) and acetonitrile (30 mL). The resulting mixture was stirred at 80° C. overnight, then cooled to room temperature and concentrated under reduced pressure. The residue was diluted with H2O (50 mL) and extracted with ethyl acetate (100 mL). The organics was washed brine (2×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:2) as the eluent to yield methyl 5-(2-(methoxymethyl)-4-methyl-1H-imidazol-5-yl)-2,4-dimethylbenzoate (compound 2.1) (0.11 g, 19%) and methyl 5-(2-(methoxymethyl)-4-methyloxazol-5-yl)-2,4-dimethylbenzoate (compound 2.2) (0.30 g, 52%), both as a yellow oils.

Aufarbeitung

  1. customInto a 100-mL round-bottom flask, was placed
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with H2O (50 mL)
  5. extractionextracted with ethyl acetate (100 mL)
  6. washThe organics was washed brine (2×50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:2) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-9f74e0ce56e449ccaa18059fe1faa499
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09428502B2

Notizen zur Reaktion

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