Hydrogen Peroxide → 4-Pentyl-4-phenyl-4-silacyclohexanone

HRID 1684444

반응식

HRID 1684444 반응식
C12BC(CCC1)CCC2.[CH2:10]([Si:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH:18]=[CH2:19])[CH:16]=[CH2:17])[CH2:11][CH2:12][CH2:13][CH3:14].Cl[CH:27]([O:29]C)Cl.CC(C)([O-])C.[Li+].[OH-].[Na+].OO.C12C(=O)C(CCC1)CCC2>O.C(O)C.CCCCCC.O1CCCC1.CO.CCCCCC>[CH2:10]([Si:15]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:18][CH2:19][C:27](=[O:29])[CH2:17][CH2:16]1)[CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

13

반응물 7

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 21004Methane, dichloromethoxy-HCID 789669-Borabicyclo(3.3.1)nonaneHCID 86638Bicyclo(3.3.1)nonan-9-oneHCID 19039141n-PentylphenyldivinylsilaneHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

생성물 1

HCID 110762054-Pentyl-4-phenyl-4-silacyclohexanone수율 91%

시약·촉매·용매 5

HCID 702Ethanol용매HCID 887Methanol용매HCID 962Water용매HCID 8058Hexane용매HCID 21883165Tetrahydrofuran hexane용매

반응 조건

온도
0 °C

실험 절차

A mixture of 15.9 g of 9-borabicyclo [3.3.1] nonan, 14.8 g of n-pentylphenyldivinylsilane and 150 ml of n-hexane was refluxed for 2 hours and then cooled with ice water. 7.0 ml of borane-dimethylsufide was added to the mixture, which was then heated again and refluxed for 2 hours. After cooling, 16 ml of methanol was added at room temperature and the mixture was stirred for 2 hours at 0° C. 25.0 g of dichloromethylmethyl ether was then dripped into the mixture, followed by also dripping a hexane-tetrahydrofuran (1:1) solution of 1.33M lithium t-butoxide into the mixture. After stirring at room temperature for 2 hours, 80 ml of ethanol, 10 ml of water and 10.0 g of sodium hydroxide were added. Then 80 ml of an aqueous solution of 30% hydrogen peroxide was slowly added. After stirring at room temperature for 2 hours, the organic layer was dried/concentrated to obtain a mixture of the target product and bicyclo [3.3.1] nonan-9-one. They were separated by means of silica-gel chromatography to obtain 15.2 g (yield 91%) of the target product. The target product thus obtained exhibited the same spectra as those of Example 7.

후처리

  1. temperaturewas refluxed for 2 hours
  2. temperaturewas then heated again
  3. temperaturerefluxed for 2 hours
  4. temperatureAfter cooling
  5. stirringAfter stirring at room temperature for 2 hours
  6. stirringAfter stirring at room temperature for 2 hours
  7. concentrationthe organic layer was dried/concentrated
  8. customto obtain
  9. customThey were separated by means of silica-gel chromatography

출처 및 근거

ORD 기록
ord-f175e89148cd417692d0144a07b154ff
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05641431

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