Benzyl Alcohol → 4-(Benzyloxy)pyridine N-oxide

HRID 15029

Reaction equation

HRID 15029 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+]([C:14]1[CH:19]=[CH:18][N+:17]([O-:20])=[CH:16][CH:15]=1)([O-])=O>CN(C=O)C>[CH2:3]([O:10][C:14]1[CH:19]=[CH:18][N+:17]([O-:20])=[CH:16][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 143004-Nitropyridine N-oxideHCID 24758Sodium hydride

Product 1

HCID 2958714-(Benzyloxy)pyridine N-oxideYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF suspension (200 mL) of sodium hydride (60% oilyness, 7.50 g, 0.188 mmol), benzyl alcohol (20.3 mL) was added under cooling with ice, and stirred for an hour at room temperature. Then 4-nitropyridine 1-oxide (25.5 g, 182 mmols) was added little by little under stirring, followed by an hour's stirring at room temperature. The solvent was concentrated under reduced pressure and chloroform (1 L) was added to the resulting residue. The insoluble matter was filtered using Celite (100 g). The filtrate was concentrated and to which acetone was added to provide the title compound (24.8 g, 69%).

Workup

  1. temperatureunder cooling with ice
  2. stirringunder stirring
  3. waitfollowed by an hour
  4. stirring's stirring at room temperature
  5. concentrationThe solvent was concentrated under reduced pressure and chloroform (1 L)
  6. additionwas added to the resulting residue
  7. filtrationThe insoluble matter was filtered
  8. concentrationThe filtrate was concentrated and to which acetone
  9. additionwas added

Sources & evidence

ORD record
ord-c43af34c914f4fb79783195755e66732
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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