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

HRID 349188

反応式

HRID 349188 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d2d972f07ced4957a4a3b7a80c7e1b08
出典データセット
uspto-grants-2007_02
特許番号
US07179807B2

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