Sodium Hydroxide → HCID 19756139, compound

HRID 1587697Notes

Reaction equation

HRID 1587697 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][CH2:16][CH2:17][CH3:18])[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][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19756108HCID 19756108, compound

Product 1

HCID 19756139HCID 19756139, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6.85 g (27 mmol) of 2-acetoxymethyl-6-hexyloxypyridine dissolved in 20 ml of ethanol was charged 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 column chromatography (ethyl acetate:hexane=1:3) to give 5.13 g of the desired product (yield 89.9%).

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 column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-18773ed70aad46468e481b332481c6b9
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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