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

HRID 349188

반응식

HRID 349188 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d2d972f07ced4957a4a3b7a80c7e1b08
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179807B2

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