N-methoxy-N-methyl-4-biphenylacetamide → 2-([1,1'-Biphenyl]-4-yl)-1-phenylethanone

HRID 401140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401140
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8](N(OC)C)=[O:9])=[CH:3][CH:2]=1.[C:20]1([Mg]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:9])=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 17815837N-methoxy-N-methyl-4-biphenylacetamideHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 2967612-([1,1'-Biphenyl]-4-yl)-1-phenylethanoneAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under N2, to a mixture of 2-(biphenyl-4-yl)-N-methoxy-N-methylacetamide (500 mg, 1.96 mmol) in anhydrous THF was added phenylmagnesium bromide (5 mL, 5 mmol) at −78° C., and the mixture was stirred for 3 hours. When TLC indicated that the starting material was consumed, the reaction mixture was diluted with EtOAc, washed with water and brine, concentrated, and purified by column chromatography (PE:EtOAc=20:1) to give Intermediate 5 (430 mg, yield 80.7%).

Aufarbeitung

  1. customwas consumed
  2. additionthe reaction mixture was diluted with EtOAc
  3. washwashed with water and brine
  4. concentrationconcentrated
  5. custompurified by column chromatography (PE:EtOAc=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-17cfa0f7bdbc4cc7b5904e1b549d4a8f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741915B2

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