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

HRID 378187
ノート
印刷プレビュー

反応式

HRID 378187 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2 回HCID 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 19352669E-6-hydroxy-1-heptenyldihydroxyborane

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d65ca18f98444c3692338a13a5013ec4
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06030546

反応ノート

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