N-Methoxy-N-methylbenzamide → 1-Phenyl-2-(4-(methylthio)phenyl)ethanone

HRID 741679

Reaktionsgleichung

Reaktionsgleichung von HRID 741679
CON(C)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:13][S:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][Mg]Cl)=[CH:17][CH:16]=1>C1COCC1>[C:5]1([C:4](=[O:11])[CH2:19][C:18]2[CH:22]=[CH:23][C:15]([S:14][CH3:13])=[CH:16][CH:17]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 569575N-Methoxy-N-methylbenzamideHCID 178503173HCID 178503173, Verbindung

Produkt 1

HCID 220095571-Phenyl-2-(4-(methylthio)phenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold (0° C.) solution of N-methoxy-N-methylbenzamide (409 mg, 2.27 mmol) in THF (22mL) was added a THF solution (5.0 mL, 0.5M) of 4-(methylthio)benzylmagnesium chloride (J.Org. Chem. 42, 1914, 1977). The mixture was stirred at 0 ° C. for 3 h. NH4OAc was added and the mixture was extracted with EtOAc. The EtOAc extracts were washed with brine, dried over MgSO4, filtered and concentrated to an oil. Chromatography of the oil on silica gel (eluted with 2.5 % EtOAc/toluene) gave 501 mg of the title compound.

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc
  2. washThe EtOAc extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil

Quellen und Nachweise

ORD-Eintrag
ord-5f5e8e8e3d2643388350f86374a0bebe
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552422

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