Ethyl Acetate → HCID 178499169, compound

HRID 1396387Notes

Reaction equation

HRID 1396387 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4](=[N+:12]=[N-:13])[C:5](=[O:11])[CH2:6][C:7](OC)=[O:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>C(OCC)C>[CH3:1][O:2][C:3]([C:4]1[N:12]=[N:13][C:7]([OH:8])=[CH:6][C:5]=1[OH:11])=[O:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 86024925HCID 86024925, compound

Product 1

HCID 178499169HCID 178499169, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-diazo-3-oxo-pentanedioic acid dimethyl ester (50.0 g, 249.8 mmol) and triphenylphosphine (65.5 g, 249.8 mmol) in diethyl ether (500 mL) was stirred at room temperature for 24 h. The organic solvent was removed under vacuum and then acetic acid (500 mL) and water (50 mL) were added to the residue and the mixture was refluxed for 10 h. The reaction mixture was concentrated under reduced pressure to obtain a viscous residue. Trituration with ethyl acetate generated a yellow solid that was purified by chromatography (silica, 100-200 mesh, 1-5% methanol in dichloromethane) to give 4,6-dihydroxy-pyridazine-3-carboxylic acid methyl ester (12.8 g, 30%) as a yellow solid. LC-MS 169.2 [M+H]+.

Workup

  1. customThe organic solvent was removed under vacuum
  2. additionacetic acid (500 mL) and water (50 mL) were added to the residue
  3. temperaturethe mixture was refluxed for 10 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customto obtain a viscous residue
  6. customthat was purified by chromatography (silica, 100-200 mesh, 1-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6eec167371c9432796fd271f9f75b9c7
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

Loading…