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1H-Indole-3-propanoic acid → 3-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-indol-3-yl]propanoic acid

HRID 590394
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HRID 590394 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1.[H-].[Na+].Br[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[Si:21]([O:20][CH2:19][CH2:18][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]
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참가 물질

6

반응물 4

HCID 37441H-Indole-3-propanoic acidHCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

생성물 1

HCID 1317344743-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-indol-3-yl]propanoic acid수율 43%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

To a solution of 3-(1H-indol-3-yl)propanoic acid (5 g, 0.026 mol) in DMF (20 mL) was added at 0° C. sodium hydride (2.11 g, 0.088 mol), the mixture was stirred some minutes at 0° C. and (2-bromoethoxy)(tert-butyl)dimethylsilane (5.67 mL, 0.026 mol) was added. The reaction mixture was stirred overnight at room temperature. The crude mixture was poured into a sodium sulphate saturate solution and extracted with ethyl acetate. The solvent was removed under reduced pressure and the crude obtained was purified over silica gel eluting with hexane:ether (100/0 to 0/100) to obtain the title compound (4g, 43%).

후처리

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. concentrationsaturate solution
  3. extractionextracted with ethyl acetate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude obtained
  6. customwas purified over silica gel eluting with hexane

출처 및 근거

ORD 기록
ord-de41a1b113eb4effa11a5b104d3582c9
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09233108B2

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