Benzyl Alcohol → 6-Benzyloxy-2-picoline 1-oxide

HRID 443286Notes

Reaction equation

HRID 443286 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N+:13]=1[O-:19]>CS(C)=O>[CH2:3]([O:10][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N+:13]=1[O-:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 45797722-Chloro-6-methylpyridine 1-oxide

Product 1

HCID 197444346-Benzyloxy-2-picoline 1-oxide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a slurry of sodium hydride (4.2 g, 105 mmol; 60% dispersion in mineral oil) in anhydrous dimethyl sulfoxide (70 mL), benzyl alcohol (8.7 mL, 84 mmol) was added over a period of 10 minute. The mixture was stirred at room temp. for 10 h., and treated with a solution of 2-chloro-6-methylpyridine N-oxide (10 g, 70 mmol) in dimethyl sulfoxide (10 mL). The resultant mixture was stirred at room temp. overnight, quenched with water and aqueous hydrochloric acid (to pH 8). The mixture was extracted with chloroform. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 1-4% methanol in chloroform gradient. Collection and concentration of appropriate fractions provided 2-benzyloxy-6-methylpyridine N-oxide as pale brown oil.

Workup

  1. customquenched with water and aqueous hydrochloric acid (to pH 8)
  2. extractionThe mixture was extracted with chloroform
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-f714cfcdf2af414eb5d2859d65b81347
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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