Ethanol → Ethyl 6-(hydroxymethyl)pyridine-3-carboxylate

HRID 1030512Notes

Reaction equation

HRID 1030512 reaction equation
C([O:4][CH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=1)(=O)C.C(O)C.[O-]CC.[Na+].[Na]>C(Cl)(Cl)Cl.C(O)(=O)C.O>[OH:4][CH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=1

Participants

8

Reactant 4

HCID 702Ethanol2×HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 15045503Ethyl 6-acetoxymethylnicotinate

Product 1

HCID 15045504Ethyl 6-(hydroxymethyl)pyridine-3-carboxylateYield 68.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 9.2 g of ethyl 6-acetoxymethylnicotinate in chloroform (40 ml) was added an ethanol solution of sodium ethoxide prepared from 0.92 g of sodium and 23 ml of ethanol, and the mixture was stirred at room temperature for 2 hours. The reaction liquid was poured into water containing 6 ml of acetic acid and the chloroform layer was separated and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure, carbon tetrachloride was added to the residue, and the insoluble substance was removed by filtration. The filtrate was concentrated under reduced pressure and the residue was recrystallized from ethyl acetate/hexane to obtain 5.1 g of ethyl 6-hydroxymethylnicotinate. ##STR8##

Workup

  1. customThe reaction liquid
  2. customthe chloroform layer was separated
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure, carbon tetrachloride
  5. additionwas added to the residue
  6. customthe insoluble substance was removed by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4e6f9bf190d0441196540707528dd407
Source dataset
uspto-grants-1992_04
Patent number
US05106859

Reaction notes

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