Water → 5-(Benzyloxy)-2-methylpyridine

HRID 1671659Notes

Reaction equation

HRID 1671659 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>CN(C)C=O>[CH2:9]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[N:4][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7503Benzyl ChlorideHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 123972515-(Benzyloxy)-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-6-methylpyridine (140 g) was dissolved in dimethylformamide (1.4 L), and with cooling with ice, benzyl chloride (178 ml) was added to it, and stirred overnight at room temperature. The reaction liquid was poured into water with ice, extracted with ethyl acetate, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=40/1 to 2/1) to obtain the entitled compound as an orange oil.

Workup

  1. additionwas added to it
  2. customThe reaction liquid
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with saturated saline water
  5. customAfter dried
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=40/1 to 2/1)

Sources & evidence

ORD record
ord-92cd6a6c72784d7aaaa90ea51ebe2d68
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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