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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
ノート
印刷プレビュー

反応式

HRID 590394 の反応式
[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]
参加物反応条件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 37441H-Indole-3-propanoic acidHCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-de41a1b113eb4effa11a5b104d3582c9
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09233108B2

反応ノート

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