N-Methoxy-N-methyl-2-phenyl-isobutyramide → 3-Methyl-3-phenylbutan-2-one

HRID 29515Notes

Reaction equation

HRID 29515 reaction equation
CON(C)[C:4](=[O:14])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[CH3:16][Mg]Br>O1CCCC1.CCCCCCC>[CH3:6][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[C:4](=[O:14])[CH3:16]

Participants

5

Reactant 2

HCID 59788661N-Methoxy-N-methyl-2-phenyl-isobutyramideHCID 178418573HCID 178418573, compound

Product 1

HCID 2854623-Methyl-3-phenylbutan-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

To 2.1 g (10.1 mmol) of N-Methoxy-N-methyl-2-phenyl-isobutyramide in 80 ml of dry tetrahydrofuran at ambient temperature was added 6.7 ml (20.2 mmol) of 3M methymagnesium bromide in heptane, and the solution was warmed to 60° C. After 6 hours, the mixture was allowed to cool to ambient temperature and was quenched with 1M HCl. The resulting mixture was partitioned between water and ether, and the phases were separated. The ether phase was washed once each with 1M HCl and brine, dried over Na2SO4, filtered, and concentrated in vacuo to an oil. The oil was chromatographed to give the title compound as a clear oil: 1H NMR CDCl3 δ (ppm): 1.49 (s, 6H), 1.93 (s, 3H), 7.24-7.34 (m, 5H).

Workup

  1. temperatureto cool to ambient temperature
  2. customwas quenched with 1M HCl
  3. customThe resulting mixture was partitioned between water and ether
  4. customthe phases were separated
  5. washThe ether phase was washed once each with 1M HCl and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to an oil
  9. customThe oil was chromatographed

Sources & evidence

ORD record
ord-e9265383be5045c8903f8dcb46c84093
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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