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Hydrogen Peroxide → 5-Decyloxy-2-{4-(6-hydroxy-1-trans-heptenyl)-phenyl}-pyrimidine

HRID 378187
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HRID 378187 반응식
[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+].[OH:27][CH:28]([CH3:37])[CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]/B(O)O.OO>O1CCCC1>[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21](/[CH:33]=[CH:32]/[CH2:31][CH2:30][CH2:29][CH:28]([OH:27])[CH3:37])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2회HCID 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 19352669E-6-hydroxy-1-heptenyldihydroxyborane

생성물 1

HCID 193525205-Decyloxy-2-{4-(6-hydroxy-1-trans-heptenyl)-phenyl}-pyrimidine수율 82%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

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 6.6 g (17 mmol) of 5-decyloxy-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-hydroxy-1-heptenyldihydroxyborane 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 5.9 g (yield 82%) of 5-decyloxy-2-{4-(6-hydroxy-1-trans-heptenyl)-phenyl}-pyrimidine.

후처리

  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

출처 및 근거

ORD 기록
ord-d65ca18f98444c3692338a13a5013ec4
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06030546

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