Dimethylformamide → 5-(Benzyloxy)-2-methylpyridine

HRID 1913275Notes

Reaction equation

HRID 1913275 reaction equation
[H-].[Na+].CN(C)C=O.[CH3:8][C:9]1[N:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)(=O)C.O>[CH2:16]([O:15][C:12]1[CH:11]=[CH:10][C:9]([CH3:8])=[N:14][CH:13]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 123972515-(Benzyloxy)-2-methylpyridineYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (4.76 g, 119 mmol) was added to a dimethylformamide solution (100 ml) of 6-methylpyridin-3-ol (10.0 g, 91.6 mmol) under ice cooling, and this mixture was stirred for 30 minutes, followed by adding benzyl chloride (12.7 ml, 110 mmol) to the mixture and stirring it for 12 hours at room temperature. Water and a saturated saline solution (1:1) and ethyl acetate were added to this reaction solution, and the solution was extracted. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 1:2) to obtain 5-(benzyloxy)-2-methylpyridine (16.4 g, yield: 90%) as an orange-colored product.

Workup

  1. stirringstirring it for 12 hours at room temperature
  2. extractionthe solution was extracted
  3. washThe organic layer was washed with water
  4. dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 1:2)

Sources & evidence

ORD record
ord-4ee4a70d8cda4194bad7892ce466a3b0
Source dataset
uspto-grants-2013_12
Patent number
US08609699B2

Reaction notes

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