Propanal → HCID 22004561, compound

HRID 324517Notes

Reaction equation

HRID 324517 reaction equation
C(OO)(C)(C)C.[CH3:7][O:8][C:9]([C:11]1[CH:16]=[N:15][CH:14]=[CH:13][N:12]=1)=[O:10].[CH:17](=[O:20])[CH2:18][CH3:19]>O.OS(O)(=O)=O>[CH3:7][O:8][C:9]([C:11]1[CH:16]=[N:15][C:14]([C:17](=[O:20])[CH2:18][CH3:19])=[CH:13][N:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 527PropanalHCID 6410tert-Butyl hydroperoxideHCID 72662Methyl pyrazinoate

Product 1

HCID 22004561HCID 22004561, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Tert-butyl hydroperoxide (70%, 1.0 ml, 7.25 mmol) and a solution of FeSO4.7H2O (3.02 g, 10.9 mmol) in water (8 ml) were added concurrently to a solution of methyl-2-pyrazine carboxylate (250 mg, 1.81 mmol) and propionaldehyde (0.78 ml, 0.9 mmol) in H2SO4 (0.75 ml) at 0 C. The reaction was allowed to warm to room temperature and was stirred for 2 hours. Solid Na2S2O5 was added (until starch/iodide test negative) and the mixture extracted with dichloromethane. Concentration in vacuo and flash column chromatography over silica gel in ethyl acetate:hexane (15:85) yielded methyl-5-propionyl-2-pyrazinecarboxylate as a pale yellow solid (106 mg). The methyl ester was treated with LiOH (25 mg, 0.6 mmol) in tetrahydrofuran (15 ml) and water (0.5 ml). After 2 hours at room temperature the mixture was acidified with HCl (2N). Work-up followed by concentration of the organic phase in vacuo gave the title compound (92 mg).

Workup

  1. extractionthe mixture extracted with dichloromethane
  2. concentrationConcentration in vacuo and flash column chromatography over silica gel in ethyl acetate:hexane (15:85)

Sources & evidence

ORD record
ord-543177e450a948869f3b3ae2a513c4a1
Source dataset
uspto-grants-2001_04
Patent number
US06218393B1

Reaction notes

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