2,2,2-Trifluoroethanol → HCID 23110960, compound

HRID 2373684Notes

Reaction equation

HRID 2373684 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](S(C)=O)[CH:9]=[C:8]([CH3:18])[N:7]=1.[H-].[Na+].[F:21][C:22]([F:26])([F:25])[CH2:23][OH:24]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([O:24][CH2:23][C:22]([F:26])([F:25])[F:21])[CH:9]=[C:8]([CH3:18])[N:7]=1

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 23110952HCID 23110952, compound

Product 1

HCID 23110960HCID 23110960, compound

Procedure

2-[(2-Methoxyethyl)oxy]-6-methyl-4-methylsulfinyl-3-nitropyridine (1.73 g, 6.31 mmol) was dissolved in 2,2,2-trifluoroethanol (15 mL). Sodium hydride (55% in oil, 600 mg, 13.75 mmol) was added to the solution, followed by refluxing for one hour. The resultant solution was allowed to stand for cooling. Subsequently, the solution was extracted with chloroform-water. The organic layer was washed with saturated brine, followed by drying over sodium sulfate anhydrate and concentration under reduced pressure. The obtained residue was purified through silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1→n-hexane/ethyl acetate=3/1), to thereby yield 2-[(2-methoxyethyl)oxy]-6-methyl-3-nitro-4-[(2,2,2-trifluoroethyl)oxy]pyridine as a pale yellow solid (1.77 g, 91%).

Workup

  1. temperatureby refluxing for one hour
  2. temperaturefor cooling
  3. extractionSubsequently, the solution was extracted with chloroform-water
  4. washThe organic layer was washed with saturated brine
  5. dry with materialby drying over sodium sulfate anhydrate and concentration under reduced pressure
  6. customThe obtained residue was purified through silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1→n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-3674076742ca46109daec69fd0062f1f
Source dataset
uspto-grants-2008_12
Patent number
US07459552B2

Reaction notes

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