Sodium Hydroxide → 6-Butoxy-2-hydroxymethylpyridine

HRID 1587693Notes

Reaction equation

HRID 1587693 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:7]=1)(=O)C.[OH-].[Na+]>C(O)C>[CH2:13]([O:12][C:8]1[N:7]=[C:6]([CH2:5][OH:4])[CH:11]=[CH:10][CH:9]=1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 197561112-Acetoxymethyl-6-butoxypyridine

Product 1

HCID 197561166-Butoxy-2-hydroxymethylpyridineYield 108.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.89 g (21.9 mmol) of 2-acetoxymethyl-6-butoxypyridine dissolved in 20 ml of ethanol was added 20 ml of an 8% sodium hydroxide solution, and the mixture was refluxed for one hour. After removal of the ethanol under a reduced pressure, the residue was extracted with ether and separated by silica gel chromatography (ethyl acetate:hexane=1:3) to obtain 4.29 g of the desired product (yield 100%).

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. customAfter removal of the ethanol under a reduced pressure
  3. extractionthe residue was extracted with ether
  4. customseparated by silica gel chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-0f97a950c3e84156b6719898b069031e
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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