Sodium Hydroxide → (6-(Benzyloxy)pyridin-2-yl)methanol

HRID 1068472Notes

Reaction equation

HRID 1068472 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:7]=1)(=O)C.[OH-].[Na+]>CO>[CH2:13]([O:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][OH:4])[N:7]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 211934372-Acetoxymethyl-6-benzyloxypyridine

Product 1

HCID 21193214(6-(Benzyloxy)pyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-acetoxymethyl-6-benzyloxypyridine (1.65 g, 6.4 mmol) and aqueous sodium hydroxide (0.58 mL, 40%) in methanol (10 mL) was stirred at room temp. overnight. The resulting solution was concentrated under vacuum, and the residue was partitioned between water and dichloromethane. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 0-5% ethyl acetate in chloroform gradient. Collection and concentration of appropriate fractions provided 2-benzyloxy-6-hydroxymethylpyridine as colorless oil.

Workup

  1. concentrationThe resulting solution was concentrated under vacuum
  2. customthe residue was partitioned between water and dichloromethane
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-24cd6f5817384163b8152b8df5f6f1a1
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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