Sodium hydride → HCID 15790526, compound

HRID 235052Notes

Reaction equation

HRID 235052 reaction equation
[H-].[Na+].[F:3][C:4]([F:17])([F:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1.CS([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)(=O)=O>CN(C=O)C>[F:3][C:4]([F:16])([F:17])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][O:15][C:26]2[CH:25]=[CH:24][N:23]=[CH:22][CH:27]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 986672-(Methylsulfonyl)pyridineHCID 15790525HCID 15790525, compound

Product 1

HCID 15790526HCID 15790526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of about one gram of 60% NaH (dispersion in oil) in 20 mL of dry DMF was added 5.2 g (0.023 m) of 2-[4-(2,2,2-trifluoroethoxy)phenyl]ethanol. The mixture was stirred at room temperature for 40 minutes, then 3.1 g (0.02 m) of methylsulfonyl pyridine was added. The mixture was stirred at room temperature overnight, then DMF was evaporated in vacuo, and the residue was diluted with water and extracted with CH2Cl2. The CH2Cl2 layer was separated, washed with saturated NaCl solution and filtered through phase separating paper. The product was concentrated to yield 6.2 g of crude product, which was adsorbed onto silica gel and chromatographed over silica gel 60 (230-400 mesh) using CH2Cl2 →50% EtOAc/CH2Cl2 to give the title product as an oil. Yield 2.5 g.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customDMF was evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with CH2Cl2
  5. customThe CH2Cl2 layer was separated
  6. washwashed with saturated NaCl solution
  7. filtrationfiltered through phase
  8. customseparating paper
  9. concentrationThe product was concentrated
  10. customto yield 6.2 g of crude product, which
  11. customchromatographed over silica gel 60 (230-400 mesh)

Sources & evidence

ORD record
ord-85feb9bc555f4bc580dc5917a059b21b
Source dataset
uspto-grants-1997_01
Patent number
US05597836

Reaction notes

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