Sodium hydride → 4-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxide

HRID 2202841Notes

Reaction equation

HRID 2202841 reaction equation
[H-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1.Cl[C:16]1[CH:21]=[CH:20][N+:19]([O-:22])=[CH:18][CH:17]=1>C1COCC1>[F:3][C:4]([F:13])([F:14])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][O:12][C:16]2[CH:21]=[CH:20][N+:19]([O-:22])=[CH:18][CH:17]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 676844-(Trifluoromethyl)benzenemethanolHCID 707244-chloropyridine N-oxide

Product 1

HCID 686576494-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxideYield 28.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of NaH (40% oil dispersion, 231 mg) in THF (10 ml) was added (4-(trifluoromethyl)phenyl)methanol (815 mg) at 0° C. The reaction mixture was stirred at the same temperature for 10 min followed by the addition of 4-chloropyridine 1-oxide (500 mg) at 0° C. The resulting reaction mixture was stirred for 1 h at 0° C. and then warmed to room temperature. After 2 h, the reaction mixture was poured into ice-water and extracted with DCM twice. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the title compound (300 mg) as a yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 1 h at 0° C.
  3. waitAfter 2 h
  4. extractionextracted with DCM twice
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a311da62e3cb44e2928d6c5569c0b552
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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