HCID 58231453, compound → HCID 58231449, compound

HRID 2381265Notes

Reaction equation

HRID 2381265 reaction equation
CON(C)[C:4](=[O:16])[CH2:5][CH2:6][C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=1[Cl:15].[CH3:18][Mg]I>C1COCC1>[Cl:15][C:8]1[CH:9]=[C:10]([Cl:14])[CH:11]=[C:12]([Cl:13])[C:7]=1[CH2:6][CH2:5][C:4](=[O:16])[CH3:18]

Participants

4

Reactant 2

HCID 58231453HCID 58231453, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 58231449HCID 58231449, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred and cold solution (0° C.) of N-methoxy-N-methyl-3-(2,4,6-trichloro-phenyl)-propionamide (1 g, 3.37 mmol) in THF (15 ml) kept under nitrogen atmosphere, MeMgI (1.3 mL of 3M ether solution, 3.9 mmole) was added and stirring was continued at 0° C. for 2 hours. Reaction mixture was quenched with 5% of HCl (10 ml) at 0° C. and aqueous layer was extracted with EtOAc (3×30 ml). The combined organic layer was washed with 20 ml of brine and dried over sodium sulfate; concentrated under vacuum to give off-white solid. The residue was purified by chromatography over silica gel. 0.50 g (60.0% of theory) of 4-(2,4,6-trichloro-phenyl)-butan-2-one was obtained in form of a solid.

Workup

  1. stirringstirring
  2. customReaction mixture
  3. customwas quenched with 5% of HCl (10 ml) at 0° C.
  4. extractionaqueous layer was extracted with EtOAc (3×30 ml)
  5. washThe combined organic layer was washed with 20 ml of brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customto give off-white solid
  9. customThe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-be22f3f47f6141f6a926ec263c41b39b
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

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