Potassium Hydroxide → Ethyl-2-[2-(hydroxymethyl)-pyridin-3-yl]-acetate

HRID 747371Notes

Reaction equation

HRID 747371 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:7]([CH2:12][O:13]C(=O)C)=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].[OH-].[K+]>CCO>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:7]([CH2:12][OH:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15169526Ethyl-2-[2-(acetoxymethyl)-pyridin-3-yl]-acetate

Product 1

HCID 22018768Ethyl-2-[2-(hydroxymethyl)-pyridin-3-yl]-acetateYield 52.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl-2-[2-(acetoxymethyl)-pyridin-3-yl]-acetate (prepared from 2-methylnicotinic acid as described by Y. Sato et al., Chem. Pharm. Bull.; EN. 1960, 8, 427) (2.37 g, 10 mmol) in EtOH (50 mL) was added KOH (3 g, 53 mmol) and the mixture stirred at reflux overnight. The mixture was cooled, concentrated under reduced pressure and diluted with brine (5 mL) and CH2Cl2 (25 mL). The aqueous phase was extracted with CH2Cl2 (2×20 mL), the phases separated and the combined organic extracts dried (Na2SO4), filtered and concentrated to afford ethyl-2-[2-(hydroxymethyl)-pyridin-3-yl]-acetate (1.03 g, 52%).

Workup

  1. temperatureat reflux overnight
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with brine (5 mL) and CH2Cl2 (25 mL)
  5. extractionThe aqueous phase was extracted with CH2Cl2 (2×20 mL)
  6. customthe phases separated
  7. dry with materialthe combined organic extracts dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0041cc7d115e4f23a0a09b66155ca8a1
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Reaction notes

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