Ethanol → 1262803-60-0

HRID 1486645Notes

Reaction equation

HRID 1486645 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[C:12](=O)([O-])[O-].[K+].[K+].[CH3:18][CH2:19][OH:20]>>[CH2:19]([O:20][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 668696851262803-60-0Yield 39%

Procedure

To a slurry of methyl 5-chloropyrazine-2-carboxylate (250 mg, 1.45 mmol) in EtOH (5 mL) was added potassium carbonate (300 mg, 2.18 mmol). The resultant solution was stirred at RT for 2 hours. The mixture was concentrated. The residue was partitioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated to afford ethyl 5-ethoxypyrazine-2-carboxylate (110 mg, 39%) as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was partitioned between water and CH2Cl2
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3552ef20e501404780a856b02601cd8c
Source dataset
uspto-grants-2016_08
Patent number
US09428475B2

Reaction notes

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