Sodium hydride → HCID 15790523, compound

HRID 235050

Reaction equation

HRID 235050 reaction equation
[H-].[Na+].[F:3][C:4]([F:22])([F:21])[C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1.[H][H].CS([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)(=O)=O>CN(C=O)C>[F:3][C:4]([F:21])([F:22])[C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2924874-MethanesulfonylpyridineHCID 15790522HCID 15790522, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15790523HCID 15790523, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.2 g of 60% NaH (as an oil dispersion, 0.005 m) in 5 mL of DMF was added 1.41 g (0.005 m) of 2-[4-[4-(trifluoromethyl)phenoxy]phenyl]ethanol. The mixture was stirred at room temperature for 30 minutes, until hydrogen evolution ceased. To the mixture was then added 0.79 g (0.005 m) of 4-(methylsulfonyl)pyridine, and the mixture was stirred overnight am room temperature. Excess DMF was then removed in vacuo. The resulting material was diluted with water, and the product was extracted into CH2Cl2. The CH2Cl2 layer was separated and filtered through phase separating paper, then concentrated. The residue was adsorbed onto silica gel and chromatographed, eluting with CH2Cl2 →30% EtOAc/CH2Cl2. The resulting material was rechromatographed over fine-particle silica gel, eluting with CH2Cl2 →50% EtOAc/CH2Cl2. Yield 0.5 g.

Workup

  1. customam room temperature
  2. customExcess DMF was then removed in vacuo
  3. additionThe resulting material was diluted with water
  4. extractionthe product was extracted into CH2Cl2
  5. customThe CH2Cl2 layer was separated
  6. filtrationfiltered through phase
  7. customseparating paper
  8. concentrationconcentrated
  9. customchromatographed
  10. washeluting with CH2Cl2 →30% EtOAc/CH2Cl2
  11. customThe resulting material was rechromatographed over fine-particle silica gel
  12. washeluting with CH2Cl2 →50% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-2d2b9369f62147bd9152c60190b2ffeb
Source dataset
uspto-grants-1997_01
Patent number
US05597836

Linked notes

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