Dimethyl Sulfoxide → HCID 21476919, compound

HRID 2293579Notes

Reaction equation

HRID 2293579 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:4][C:3]=2[O:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CS(C)=O.Br[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][CH:43]=1>C1COCC1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH2:41][C:42]3[CH:43]=[CH:44][C:45]([C:48]([F:49])([F:50])[F:51])=[CH:46][CH:47]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 2733832Lithium HexamethyldisilazideHCID 21476920HCID 21476920, compound

Product 1

HCID 21476919HCID 21476919, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a suspension of 0.992 g (0.27 mmol) of the product of Example 1 in 0.5 mL of anhydrous THF was added 825 μL (0.82 mmol) of a 1.0M solution of lithium bis(trimethylsilyl)amide in THF at -78° C. under a nitrogen atmosphere. After stirring at -78° C. for 10 minutes, the starting material had not fully dissolved. The reaction mixture was then warmed to 0° C. (ice-water bath) and 300 μL of DMSO was added which resulted in a clear yellow solution, then 0.131 g (0.55 mmol) of α'-bromo-α,α,α-trifluoro-p-xylene was added as a solid. Stirring was maintained for 1 hour, then the reaction mixture was partitioned between EtOAc and water and extracted. The organic layer was washed with saturated brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 2.5% MeOH--CHCl3. Evaporation of the product fractions and drying in vacuo afforded 0.040 g (28%) of the title compound.

Workup

  1. dissolutionthe starting material had not fully dissolved
  2. additionwas added which
  3. customresulted in a clear yellow solution
  4. stirringStirring
  5. temperaturewas maintained for 1 hour
  6. customthe reaction mixture was partitioned between EtOAc and water
  7. extractionextracted
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified on a silica gel flash chromatography column
  13. washeluted with 2.5% MeOH
  14. customEvaporation of the product fractions
  15. customdrying in vacuo

Sources & evidence

ORD record
ord-17f07d8ce02448cb879640cfe7d7c92a
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

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