Reaction #64869

Reaction equation

glyoxylic acid monohydrate

propargyl alcohol

ammonium acetate

→

2-amino-5-hydroxy-3-pentynoic acid

Solvents

ethanol

Conditions

Workup

1. 1
   Temperatureis heated
2. 2
   Temperatureunder reflux for 6 h
3. 3
   ConcentrationThen the reaction mixture is concentrated in vacuo
4. 4
   workup.ADDITIONdiluted with water (50 ml)
5. 5
   Washwashed twice with ether (100 ml)
6. 6
   workup.ADDITIONThen the aqueous solution is poured on an ion exchange resin column (DOWEX 50, H+) The column
7. 7
   Washis eluted with 1M ammonium hydroxide

Procedure

A mixture of glyoxylic acid monohydrate (23 g, 250 mmol), propargyl alcohol (16.8 g, 300 mmol ), copper (II) chloride (3.2 g, 25 mmol) and ammonium acetate (49 g, 600 mmol) in ethanol (100 ml) is heated under reflux for 6 h. Then the reaction mixture is concentrated in vacuo, diluted with water (50 ml), acidified to pH 5 with 1N HCl and washed twice with ether (100 ml). Then the aqueous solution is poured on an ion exchange resin column (DOWEX 50, H+) The column is eluted with 1M ammonium hydroxide to give the title compound 2-amino-5-hydroxy-3-pentynoic acid.

Source