Water → 5-(Benzyloxy)-2-methylpyridine

HRID 2080692Notes

Reaction equation

HRID 2080692 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

140 g of 3-hydroxy-6-methylpyridine was dissolved in 1.4 L of dimethylformamide, and with cooling with ice, 178 ml of benzyl chloride 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 246.7 g of 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-8fd37e848d2d473fa8bef9f6ce363b20
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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