Ethyl Acetate → HCID 13186545, Verbindung

HRID 924945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924945
CON(C)[C:4]([C:6]1[CH:10]=[CH:9][O:8][CH:7]=1)=[O:5].[CH2:12]([Mg]Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOC(C)=O.[NH4+].[Cl-]>C1COCC1>[O:8]1[CH:9]=[CH:10][C:6]([C:4](=[O:5])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 10487090N-methoxy-N-methylfuran-3-carboxamideHCID 178418336HCID 178418336, Verbindung

Produkt 1

HCID 13186545HCID 13186545, VerbindungAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of N-methoxy-N-methylfuran-3-carboxamide (913 mg, 5.89 mmol) in anhydrous THF (10 mL) was cooled to −78° C. under nitrogen, and a solution of benzylmagnesium chloride in THF (2 mol/L, 3.53 mL) was added through a syringe. The reaction mixture was stirred at this temperature for 5 hours. TLC (PE:EtOAc=5:1) indicated reaction was nearly complete, saturated NH4Cl solution (20 mL) was added to quench the reaction, and the aqueous layer was extracted with EtOAc (80 mL). The organic layer was washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated to afford 1-(furan-3-yl)-2-phenylethanone as a yellow oil (696 mg, yield: 63.2%).

Aufarbeitung

  1. customreaction
  2. customto quench
  3. customthe reaction
  4. extractionthe aqueous layer was extracted with EtOAc (80 mL)
  5. washThe organic layer was washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2af9adb1692a45f592c54689f9c8b6c7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283229B2

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