Acetic Acid → Ethyl 3-hydroxy-2-(hydroxymethyl)-2-(pyridin-3-yl)propanoate

HRID 64441Notes

Reaction equation

HRID 64441 reaction equation
C(O[C:5]1[C:6](CC)=[N:7][CH:8]=[CH:9][CH:10]=1)(=O)C.[CH2:13]=[O:14].[O-][CH2:16][CH3:17].[Na+].[C:19]([OH:22])(=[O:21])[CH3:20].CN([CH:26]=[O:27])C>>[OH:14][CH2:13][C:20]([CH2:26][OH:27])([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[C:19]([O:22][CH2:16][CH3:17])=[O:21]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 6228DimethylformamideHCID 2723922Sodium ethoxideHCID 671213462-Ethylpyridin-3-yl acetate

Product 1

HCID 86713459Ethyl 3-hydroxy-2-(hydroxymethyl)-2-(pyridin-3-yl)propanoate

Procedure

To a solution of 2 g of ethylpyridin-3-yl acetate in 40 ml of DMF were added 1.09 g of paraformaldehyde and 165 mg of sodium ethoxide, followed by stirring for 19 hours. Acetic acid was added thereto under ice-cooling and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.29 g of ethyl 3-hydroxy-2-(hydroxymethyl)-2-(pyridin-3-yl)propanoate.

Workup

  1. temperatureunder ice-cooling
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c423c256e75e469896da3a8ae76155aa
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

Loading…