Magnesium → 1,1,1-Trifluoro-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]pentan-2-one

HRID 2106030Notes

Reaction equation

HRID 2106030 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[Mg].[F:15][C:16]([F:24])([F:23])[C:17](=[O:22])[CH:18]=[C:19]([CH3:21])[CH3:20]>C1COCC1>[F:15][C:16]([F:24])([F:23])[C:17](=[O:22])[CH2:18][C:19]([CH3:21])([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)[CH:3]=1)[CH3:20]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 109992182-(3-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 220326911,1,1-Trifluoro-4-methylpent-3-en-2-one

Product 1

HCID 578100111,1,1-Trifluoro-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]pentan-2-oneYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(3-bromophenyl)-2-methyl-[1,3]dioxolane (1 g) in THF (5 mL) was added portionwise magnesium metal (0.2 g) and the reaction heated at refluxed for 30 minutes. The mixture was cooled to room temperature and CuBr-DMS complex (846 mg, 4.11 mmol) was added. The mixture was stirred 3 minutes at room temperature, cooled to 0° C. and 1,1,1-trifluoro-4-methylpent-3-en-2-one (62 mg, 4.11 mmol) in 20 mL of THF was added dropwise. The mixture was stirred for 30 minutes at 0° C., warmed to room temperature, stirred overnight and quenched with aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford a residue that was purified by flash chromatography. Concentration in vacuo of the product-rich fractions afforded 0.56 g of 1,1,1-trifluoro-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]pentan-2-one.

Workup

  1. temperaturethe reaction heated
  2. temperatureat refluxed for 30 minutes
  3. additionCuBr-DMS complex (846 mg, 4.11 mmol) was added
  4. temperaturecooled to 0° C.
  5. stirringThe mixture was stirred for 30 minutes at 0° C.
  6. temperaturewarmed to room temperature
  7. stirringstirred overnight
  8. customquenched with aqueous ammonium chloride solution and ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customto afford a residue that
  13. customwas purified by flash chromatography
  14. concentrationConcentration in vacuo of the product-rich fractions

Sources & evidence

ORD record
ord-54c66c38ed9e4981a87770784dc34b94
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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