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1,6-Dibromohexane → {2-[(6-Bromohexyl)oxy]ethoxy}(tert-butyl)dimethylsilane

HRID 218993
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HRID 218993 반응식
[Si:1]([O:8][CH2:9][CH2:10][OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]
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참가 물질

6

반응물 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanol

생성물 1

HCID 46831953{2-[(6-Bromohexyl)oxy]ethoxy}(tert-butyl)dimethylsilane수율 67.1%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매
HCID 962
Water
용매

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온도
20 °C

실험 절차

2-{[tert-Butyl(dimethyl)silyl]oxy}ethanol (1.82 g), 1,6-dibromohexane (7.56 g) and tetrabutylammonium bromide (0.067 g) were stirred under nitrogen and treated with 50% w/v sodium hydroxide (2 g in 4 ml). The mixture was stirred vigorously at 20° C. for 5 days. Water (100 ml) was added, and the product extracted with dichloromethane (3×50 ml). The combined organic layer was separated and dried over Na2SO4 before filtering. The solvent was evaporated in vacuo to give a residue which was purified by flash chromatography on silica. Elution with 5% ether/cyclohexane followed by solvent evaporation in vacuo gave the title compound (2.35 g). LCMS RT=4.32 min, ES+ve 339 (MH)+.

후처리

  1. extractionthe product extracted with dichloromethane (3×50 ml)
  2. customThe combined organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationbefore filtering
  5. customThe solvent was evaporated in vacuo
  6. customto give a residue which
  7. customwas purified by flash chromatography on silica
  8. washElution with 5% ether/cyclohexane
  9. customfollowed by solvent evaporation in vacuo

출처 및 근거

ORD 기록
ord-4c133703382a485a89c25e262e55fada
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08198483B2

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