Hydrogen Peroxide → 1-[3,6-Diethyl-5-(2-methylbutyl)pyrazin-2-yl]-2,4-dimethoxybenzene

HRID 349188

Reaction equation

HRID 349188 reaction equation
C12BC(CCC1)CCC2.[CH3:10][C:11]([CH2:13][CH3:14])=[CH2:12].Br[C:16]1[N:17]=[C:18]([CH2:34][CH3:35])[C:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])=[N:20][C:21]=1[CH2:22][CH3:23].[OH-].[Na+].OO>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:34]([C:18]1[C:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])=[N:20][C:21]([CH2:22][CH3:23])=[C:16]([CH2:10][CH:11]([CH3:12])[CH2:13][CH3:14])[N:17]=1)[CH3:35]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 112402-Methyl-1-buteneHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 222491451-(5-Bromo-3,6-diethylpyrazin-2-yl)-2,4-dimethoxybenzene

Product 1

HCID 222489491-[3,6-Diethyl-5-(2-methylbutyl)pyrazin-2-yl]-2,4-dimethoxybenzeneYield 57.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9-BBN (9-borabicyclo[3.3.1]nonane) in THF (0.5 M, 6.0 mL, 3.0 mmol) is added to a solution of 2-methyl-1-butene (210 mg, 3.0 mmol) in THF. The mixture is heated at reflux, under a nitrogen atmosphere for 12 hours and cooled. 1-(5-Bromo-3,6-diethylpyrazin-2-yl)-2,4-dimethoxybenzene (664 mg, 2.0 mmol), tetrakis(triphenylphosphine) palladium(0) (50 mg), and sodium hydroxide (3.0 M, 3.0 mL, 3.0 mmol) are added to the solution. The mixture is heated at 50 C for 12 hours and cooled. 30% Hydrogen peroxide (1 mL) is added, the solution stirred for 1 hour and the reaction mixture extracted with ether. The combined extracts are dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography, eluting with 40% ether in hexanes to give 1-[3,6-diethyl-5-(2-methylbutyl)pyrazin-2-yl]-2,4-dimethoxybenzene (393 mg).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux, under a nitrogen atmosphere for 12 hours
  3. temperaturecooled
  4. temperatureThe mixture is heated at 50 C for 12 hours
  5. temperaturecooled
  6. extractionthe reaction mixture extracted with ether
  7. dry with materialThe combined extracts are dried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified by flash chromatography
  11. washeluting with 40% ether in hexanes

Sources & evidence

ORD record
ord-d2d972f07ced4957a4a3b7a80c7e1b08
Source dataset
uspto-grants-2007_02
Patent number
US07179807B2

Linked notes

Loading…