Ammonium Chloride → 3-Methyl-1-(3-methyl-1-benzofuran-2-yl)butan-1-one

HRID 2091004Notes

Reaction equation

HRID 2091004 reaction equation
CON(C)[C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]=1[CH3:11])=[O:5].[CH2:17]([Mg]Br)[CH:18]([CH3:20])[CH3:19].O1CCCC1.C([Mg]Br)C(C)C.[Cl-].[NH4+]>O1CCCC1>[CH3:17][CH:18]([CH3:20])[CH2:19][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]=1[CH3:11])=[O:5]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 55027902N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamideHCID 178418816HCID 178418816, compoundHCID 178420648HCID 178420648, compound

Product 1

HCID 667790263-Methyl-1-(3-methyl-1-benzofuran-2-yl)butan-1-oneYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (20 mL) of N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamide (1.00 g) synthesized above in tetrahydrofuran was added dropwise a 1.0M solution (6.84 mL) of isobutylmagnesium bromide in tetrahydrofuran at 0° C., and the mixture was stirred for 1 hr. In addition, 1.0M isobutylmagnesium bromide tetrahydrofuran solution (6.84 mL) was added, and the mixture was stirred at 0° C. for 1 hr then at room temperature for 2 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio) to give the title object compound (873 mg, 89%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hr
  2. waitat room temperature for 2 hr
  3. customto quench
  4. customthe reaction
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio)

Sources & evidence

ORD record
ord-922600a62efc47fab135ee910583aa6e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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