Hydrogen Peroxide → HCID 19352637, compound

HRID 725677Notes

Reaction equation

HRID 725677 reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-:23].[Na+].OO>O1CCCC1>[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19](/[CH:13]=[CH:16]/[CH2:17][CH2:18][CH2:19][CH:20]([O:23][C:1](=[O:9])[CH3:2])[CH3:21])=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 19352560HCID 19352560, compound

Product 1

HCID 19352637HCID 19352637, compoundYield 160.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Apart from the above, inner atmosphere of a four-necked flask equipped with a stirring device, a reflux condenser and a thermometer was replaced with nitrogen gas, and then the flask was charged with 6.2 g (17 mmol) of 5-octyloxy-2-(4-bromophenyl)-pyrimidine, 0.23 g (0.2 mmol) of tetrakis-triphenylphosphine-palladium, 2.4 g (60 mmol) of sodium hydroxide and 60 ml of tetrahydrofuran. Subsequently, 50 ml of a solution prepared by dissolving 20 mmol of the above-obtained E-6-acetoxy-1-heptenylcatecholborane in tetrahydrofuran was dropwise added thereto at room temperature. Then, the whole mixture was heated under reflux with stirring for 6 hours. After cooling the reaction mixture to room temperature, 5 ml of 10% aqueous solution of sodium hydroxide and 2 ml of 30% aqueous solution of hydrogen peroxide were added, and the resulting mixture was stirred for one hour. The mixture was extracted with ether, and the organic layer was twice washed with each 20 ml portion of saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 6.0 g (yield 78%) of 5-octyloxy-2-{4-(6-acetoxy-1-trans-heptenyl)-phenyl}-pyrimidine.

Workup

  1. customApart from the above, inner atmosphere of a four-necked flask equipped with a stirring device, a reflux condenser
  2. additionwas dropwise added
  3. customat room temperature
  4. temperatureThen, the whole mixture was heated
  5. temperatureunder reflux
  6. stirringthe resulting mixture was stirred for one hour
  7. extractionThe mixture was extracted with ether
  8. washthe organic layer was twice washed with each 20 ml portion of saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-72dd16fd40ef42c8ae97daa8fd1e74e5
Source dataset
uspto-grants-1998_01
Patent number
US05707547

Reaction notes

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