Chloroacetaldehyde → HCID 117874517, compound

HRID 2272869Notes

Reaction equation

HRID 2272869 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[Br-].[Li+].C(=O)(O)[O-].[Na+].Cl[CH2:20][CH:21]=O>CC(C)=O>[CH:3]1[C:2]2[N:1]([CH:20]=[CH:21][C:7]=2[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 1514203Methyl 2-pyrazineacetate

Product 1

HCID 117874517HCID 117874517, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 10 g (65.7 mmol) of methyl pyrazin-2-ylacetate in 263 mL of anhydrous acetone (4 mL/mmol) there are added in succession 5.7 g of lithium bromide (65.7 mmol), 22.1 g of sodium bicarbonate (263 mmol) and then 9.4 mL of chloroacetaldehyde (50% solution in water) (72.6 mmoles). The whole is subsequently heated at reflux overnight. The reaction mixture is subsequently concentrated to dryness and then taken up in ethyl acetate. The organic phase is washed with a saturated sodium chloride solution, dried over magnesium sulphate, filtered and then concentrated to dryness. There is obtained an oil, which is purified by chromatography over silica gel (CH2Cl2/ethyl acetate gradient). After concentration, the title product is obtained in the form of a solid.

Workup

  1. temperatureThe whole is subsequently heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture is subsequently concentrated to dryness
  4. washThe organic phase is washed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThere is obtained an oil, which
  9. customis purified by chromatography over silica gel (CH2Cl2/ethyl acetate gradient)
  10. concentrationAfter concentration

Sources & evidence

ORD record
ord-21fac2efb26943c98ae8dc423de42668
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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