Methyl propionate → Methyl 2-methyl-3-oxo-3-(pyrazin-2-yl)propanoate

HRID 1182345Notes

Reaction equation

HRID 1182345 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:11][CH3:12])(=[O:10])[CH2:8][CH3:9].[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[C:19](OC)=[O:20].[Cl-].[NH4+]>O1CCCC1.O>[CH3:9][CH:8]([C:19]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][N:13]=1)=[O:20])[C:7]([O:11][CH3:12])=[O:10]

Participants

7

Reactant 4

HCID 11124Methyl propionateHCID 25517Ammonium ChlorideHCID 72662Methyl pyrazinoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 11333018Methyl 2-methyl-3-oxo-3-(pyrazin-2-yl)propanoateYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1.2 L of tetrahydrofuran and 87.8 g (0.78 mole) of potassium t-butoxide were added to a reactor and cooled to 0° C. 71.5 mL (0.74 mol) of methyl propionate was dropwise added to the reactor and stirred at 0° C. for 30 minutes. 60 g (0.434 mole) of the methyl pyrazine-2-carboxylate of Example 1 dissolved in 500 mL of tetrahydrofuran was dropwise added to the reactor for 30 minutes and stirred at a temperature of 20 to 25° C. for 3 hours. 0.5 L of distilled water and 0.5 L of saturated ammonium chloride solution were added to the reaction solution and stirred for 30 minutes. The resultant reaction solution was concentrated to a volume of 1.0 L and then extracted with 1.0 L of methylenechloride. The resultant extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to give 75.0 g of the titled compound as a dark brown viscous oil (yield 89.0%).

Workup

  1. additionwas dropwise added to the reactor for 30 minutes
  2. stirringstirred at a temperature of 20 to 25° C. for 3 hours
  3. stirringstirred for 30 minutes
  4. customThe resultant reaction solution
  5. concentrationwas concentrated to a volume of 1.0 L
  6. extractionextracted with 1.0 L of methylenechloride
  7. extractionThe resultant extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bed4a1c0d784442888ba0a85d1116eff
Source dataset
uspto-grants-2007_10
Patent number
US07288652B2

Reaction notes

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