Ethyl Acetate → 2-Tert-butoxy-6-vinylpyrazine

HRID 606149Notes

Reaction equation

HRID 606149 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8](Cl)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC.C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+].O>[C:1]([O:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]([CH:13]=[CH2:14])[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 222485262-tert-Butoxy-6-chloropyrazine

Product 1

HCID 222482762-Tert-butoxy-6-vinylpyrazineYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

After dissolving 5.25 g of 2-tert-butoxy-6-chloropyrazine in 80 ml of N,N-dimethylformamide, 9.66 g of tributyl(vinyl)tin and 0.97 g of dichlorobis(triphenylphosphine) palladium (II) were added and the mixture was stirred for 8 hours and 30 minutes at 80° C. under a nitrogen atmosphere. Saturated brine and ethyl acetate were added to the reaction solution, and the insoluble portion was filtered off. The ethyl acetate layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (4.24 g, 85% yield).

Workup

  1. additionwere added
  2. filtrationthe insoluble portion was filtered off
  3. washThe ethyl acetate layer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c568718dae0a4ff08ec4d385b3cb9d23
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

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