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

HRID 443288Notes

Reaction equation

HRID 443288 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-e1bff4e0e3ad4e2381db8e3a3087689c
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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