Hydrochloric Acid → Methyl 5-(2-hydroxyethyl)pyrazine-2-carboxylate

HRID 2192919Notes

Reaction equation

HRID 2192919 reaction equation
[O:1]=[CH:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1.[BH4-].[Na+].Cl>CO.[Cl-].[Na+].O>[OH:1][CH2:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86593792Methyl 5-(2-oxoethyl)pyrazine-2-carboxylate

Product 1

HCID 59571042Methyl 5-(2-hydroxyethyl)pyrazine-2-carboxylateYield 26.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl 5-(2-oxoethyl)pyrazine-2-carboxylate (5.08 g) in methanol (50 mL) was added sodium borohydride (1.07 g) under ice-cooling, followed by stirring at the same temperature for 60 minutes. To the reaction mixture was added 1 M hydrochloric acid under ice-cooling to adjust the pH to 3. Saturated brine was added thereto, followed by extraction with a solvent (ethyl acetate:isopropyl alcohol=4:1). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-0:1, chloroform:methanol=1:0-30:1) to obtain methyl 5-(2-hydroxyethyl)pyrazine-2-carboxylate (1.34 g) as a red-brown oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with a solvent (ethyl acetate:isopropyl alcohol=4:1)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=4:1-0:1, chloroform:methanol=1:0-30:1)

Sources & evidence

ORD record
ord-dfba40980f024d3692238524b2ad25ef
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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