2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide → 3,4-Dimethoxy-2-phenylacetophenone

HRID 401144Notes

Reaction equation

HRID 401144 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](N(OC)C)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 112186512-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamideHCID 178418255HCID 178418255, compound

Product 1

HCID 123366833,4-Dimethoxy-2-phenylacetophenoneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2, to a mixture of 2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide (200 mg, 0.84 mmol) in anhydrous THF was added phenylmagnesium bromide (2.1 mL, 2.1 mmol) at −78° C., and the mixture was stirred for 2 hours. When TLC indicated that the start 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 7 (130 mg, yield 61%).

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-965734e9c55d41aca0e7282db0bdf3a5
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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