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

HRID 2254430Notes

Reaction equation

HRID 2254430 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH3:9])[N+:7]=1[O-:8].[H-].[Na+].[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(Cl)(Cl)Cl.O.CS(C)=O>[CH2:12]([O:19][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH3:9])[N+:7]=1[O-:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 45797722-Chloro-6-methylpyridine 1-oxide

Product 1

HCID 197444346-Benzyloxy-2-picoline 1-oxideYield 54%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

0.80 g of 6-chloro-2-picoline 1-oxide was added to an alcoholate solution prepared from 0.33 g of 60% oily sodium hydride, 0.69 ml of benzyl alcohol and 5 ml of dimethyl sulfoxide. The mixture was stirred overnight at room temperature. 1N-HCl (1.7 ml) was added to the reaction mixture and then water and chloroform were added. The organic layer was separated, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Wakogel C-200, 100 g; eluting solvent: chloroform/methanol=80/1→40/1) to give 0.64 g (yield 54%) of 6-benzyloxy-2-picoline 1-oxide.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe desiccant was removed by filtration
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Wakogel C-200, 100 g; eluting solvent: chloroform/methanol=80/1→40/1)

Sources & evidence

ORD record
ord-9a861057c6974702bb25e556cea2d2d4
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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