N-methoxy-N-methyl-2-(3-methylphenyl)acetamide → 2-(3-Methylphenyl)acetophenone

HRID 924927Notes

Reaction equation

HRID 924927 reaction equation
CON(C)[C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([C:4](=[O:13])[CH2:5][C:6]2[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 62873680N-methoxy-N-methyl-2-(3-methylphenyl)acetamideHCID 178418255HCID 178418255, compound

Product 1

HCID 131736142-(3-Methylphenyl)acetophenoneYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2, to a mixture of N-methoxy-N-methyl-2-m-tolylacetamide (500 mg, 2.6 mmol) in anhydrous THF was added phenylmagnesium bromide (6.5 mL, 6.5 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=30:1) to give Intermediate 4 (460 mg, yield 84.6%).

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=30:1)

Sources & evidence

ORD record
ord-bb21b123e9ff4abc9c45e41e3343e5a2
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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