Propargyl alcohol → HCID 19937323, compound

HRID 36591Notes

Reaction equation

HRID 36591 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.[CH2:7]([OH:10])[C:8]#[CH:9].C([O-])(=O)C.[NH4+:15]>C(O)C.[Cu](Cl)Cl>[NH2:15][CH:3]([C:9]#[C:8][CH2:7][OH:10])[C:2]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 517165Ammonium AcetateHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 19937323HCID 19937323, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

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.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 h
  3. concentrationThen the reaction mixture is concentrated in vacuo
  4. additiondiluted with water (50 ml)
  5. washwashed twice with ether (100 ml)
  6. additionThen the aqueous solution is poured on an ion exchange resin column (DOWEX 50, H+) The column
  7. washis eluted with 1M ammonium hydroxide

Sources & evidence

ORD record
ord-6799667dd05d48d48fc66659400e1725
Source dataset
uspto-grants-1995_05
Patent number
US05416076

Reaction notes

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