Ethylene Glycol → HCID 86593791, compound

HRID 719935Notes

Reaction equation

HRID 719935 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8](C=O)=[CH:7][N:6]=1)=[O:4].[CH2:13]([OH:16])[CH2:14][OH:15].O.[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH:18]2[O:16][CH2:13][CH2:14][O:15]2)=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 44515461Methyl 5-formylpyrazine-2-carboxylate

Product 1

HCID 86593791HCID 86593791, compoundYield 757.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-formyl-pyrazine-2-carboxylic acid methyl ester (325 mg, 1.56 mmol), ethylene glycol (100 μL, 1.79 mmol), and p-toluenesulfonic acid monohydrate (30 mg, 0.157 mmol) in benzene (10 mL) was heated under reflux with a Dean-Stark condenser for 17 h. The mixture was cooled and diluted with benzene (25 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (25 mL) and a saturated aqueous sodium chloride solution (25 mL). Each aqueous wash was back-extracted with a small portion of benzene. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 5-[1,3dioxolan-2-yl-pyrazine-2-carboxylic acid methyl ester as an orange-red oil (250 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux with a Dean-Stark condenser for 17 h
  3. temperatureThe mixture was cooled
  4. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution (25 mL)
  5. washEach aqueous wash
  6. extractionwas back-extracted with a small portion of benzene
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-964327c8bc394db3a9c239c6496e1791
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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