Potassium Hydroxide → Ethyl-2-[2-(hydroxymethyl)-pyridin-3-yl]-acetate
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
Product 1
Reagents, catalysts & solvents 1
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%).