HCID 58762226, compound → 1-(4-methoxyphenyl)pentan-3-one

HRID 858571Notes

Reaction equation

HRID 858571 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CON(C)[C:8](=[O:19])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1>C1COCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][C:8](=[O:19])[CH2:1][CH3:2])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 58762226HCID 58762226, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 2281241-(4-methoxyphenyl)pentan-3-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethylmagnesium bromide (10.8 mL, 10.8 mmol, 1M soln in THF) was added to a cooled −78° C. solution of N-Methoxy-3-(4-methoxy-phenyl)-N-methyl-propionamide (2 g, 8.96 mmol, from Step 1) dissolved in THF (20 mL). The reaction mixture was stirred for 60 min. The reaction was quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was washed brine, dried over Na2SO4 and concentrated to a clear oil. The residue was purified by silica gel chromatography (5% EtOAc in hexanes) to give the title compound as a clear oil (0.87 g, 50%).

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a clear oil
  6. customThe residue was purified by silica gel chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7fc014611fc5415ab452a71bfad19d57
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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