Ammonia → HCID 66974507, compound

HRID 1962564Notes

Reaction equation

HRID 1962564 reaction equation
[F:1][C:2](F)([CH2:12][CH:13](I)[Si](C)(C)C)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=O.[NH3:20]>O1CCCC1>[F:1][C:2]1[CH:12]=[CH:13][NH:20][C:3]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66974519HCID 66974519, compound

Product 1

HCID 66974507HCID 66974507, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 mL) of 2,2-difluoro-4-iodo-1-(2-methylphenyl)-4-trimethylsilylbutan-1-one (2.5 g) in tetrahydrofuran was added 28% aqueous ammonia solution (6 mL), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetonitrile (15 mL) and water (8 mL), and potassium fluoride (0.75 g) was added. The reaction mixture was stirred at 60° C. for 3 hr, and concentrated under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=20:1) to give the title compound as a pale-yellow oil (yield 0.87 g, 78%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in acetonitrile (15 mL)
  6. additionwater (8 mL), and potassium fluoride (0.75 g) was added
  7. stirringThe reaction mixture was stirred at 60° C. for 3 hr
  8. concentrationconcentrated under reduced pressure
  9. extractionThe residue was extracted with ethyl acetate
  10. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=20:1)

Sources & evidence

ORD record
ord-aa488138c75149d4bf826c34f440e7c7
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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