Benzyl Bromide → 5-(Benzyloxy)-2-methylpyridine

HRID 2080158Notes

Reaction equation

HRID 2080158 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[CH2:11]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[N:4][CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 123972515-(Benzyloxy)-2-methylpyridineYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxy-6-methylpyridine (5.00 g, 45.8 mmol) in N,N-dimethylformamide (50 mL) was added sodium hydride (2.02 g, 50.4 mmol, 60% in oil) at 0° C., and the solution was stirred for 15 minutes at 0° C. Then, benzyl bromide (5.99 mL, 50.4 mmol) was added at 0° C., and the solution was stirred for 3.5 hours at room temperature. The reaction solution was partitioned in water and ethyl acetate. This organic layer was separated, washed with water and brine and dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (heptane/ethyl acetate=2/1), and the title compound (5.99 g, 66%) was obtained as a colorless oil.

Workup

  1. stirringthe solution was stirred for 3.5 hours at room temperature
  2. customThe reaction solution was partitioned in water
  3. customThis organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe organic layer was filtered
  7. customthe solvent was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-6ee4d17d03dc485db0d1a918e8bd65fa
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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