Pyridine → HCID 19883544, compound

HRID 846736Notes

Reaction equation

HRID 846736 reaction equation
[CH3:1]C1(C)OC(=O)CC(=O)O1.ClCCl.N1C=CC=CC=1.Cl[C:21](=[O:39])[CH2:22][CH2:23][CH:24]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1>O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH:24]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH2:23][CH2:22][C:21](=[O:39])[CH3:1])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane3×HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 14518095HCID 14518095, compound

Product 1

HCID 19883544HCID 19883544, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 17.3 parts of 2,2-dimethyl-1,3-dioxane-4,6-dione in 130 parts of dichloromethane were added 18 parts of pyridine under nitrogen atmosphere. Then there were added dropwise, during a 20 minutes-period a solution of 35.4 parts of 1-chloro-4,4-bis(4-fluorophenyl)-1-butanone in 65 parts of dichloromethane at about 0° C. while nitrogen gas was still introduced. Upon completion, stirring was continued first for 1 hour at about 0° C. and further for 1 hour at room temperature. Dichloromethane and water were added and the layers were separated. The organic phase was washed with water, dried, filtered and evaporated. The residue was boiled in 750 parts of a mixture of acetic acid and water (1:2 by volume) for 5 hours. Methylbenzene was added. The organic phase was separated, washed with water, with a sodium hydrogen carbonate solution and again with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 18.5 parts of 5,5-bis(4-fluorophenyl)-2-pentanone as a residue (intermediate 31).

Workup

  1. additionwas still introduced
  2. customthe layers were separated
  3. washThe organic phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. additionThe residue was boiled in 750 parts of a mixture of acetic acid and water (1:2 by volume) for 5 hours
  8. additionMethylbenzene was added
  9. customThe organic phase was separated
  10. washwashed with water, with a sodium hydrogen carbonate solution and again with water
  11. customdried
  12. filtrationfiltered
  13. customevaporated
  14. customThe residue was purified by column-chromatography over silica gel
  15. customThe pure fractions were collected
  16. customthe eluent was evaporated

Sources & evidence

ORD record
ord-0f1a4cef7eb14e0dad8931e9aaf97bf7
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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