Pyridine, hydrofluoride (1:1) → HCID 72602284, compound

HRID 636744Notes

Reaction equation

HRID 636744 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[N+:10]([C:12]([CH3:23])([CH3:22])[CH2:13][O:14][Si](C(C)(C)C)(C)C)[O-:11].N1C=CC=CC=1.F.C([O-])(O)=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[N+:10]([C:12]([CH3:23])([CH3:22])[CH2:13][OH:14])[O-:11]

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 131722403HCID 131722403, compound

Product 1

HCID 72602284HCID 72602284, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of α-(2,4-difluorophenyl)-N-[dimethyl(t-butyldimethylsiloxymethyl) methyl]nitrone (688.3 mg, 2.00 mmol) in THF (20 ml) was cooled to 0° C. in ice-water bath. To the mixture was added carefully hydrogen fluoride-pyridine (1 ml). The mixture was gradually warmed to room temperature and stirred for 7 hours. The mixture was added to sat. NaHCO3 aqueous solution and extracted three times with ethyl acetate and dried over MgSO4. The solvent was evaporated and the white crystals were washed with hexane to give the title compound (317.3 mg; 69%).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated
  4. washthe white crystals were washed with hexane

Sources & evidence

ORD record
ord-6735e26b84ff4715bb6a8a174c6d8716
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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