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

HRID 2178024Notes

Reaction equation

HRID 2178024 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 2967612-([1,1'-Biphenyl]-4-yl)-1-phenylethanoneYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-8ac28736929441f4892b10ad36ebbd26
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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