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Sodium hydride → 5-Allyloxy-1-[(6-chlorobenzo[1,3]dioxol-5-yl)methyl]-1h-indole-2-carboxylic acid ethyl ester

HRID 434020
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 434020
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4].[CH2:21]1[O:25][C:24]2[CH:26]=[C:27]([Cl:32])[C:28]([CH2:30]Cl)=[CH:29][C:23]=2[O:22]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:30][C:28]2[C:27]([Cl:32])=[CH:26][C:24]3[O:25][CH2:21][O:22][C:23]=3[CH:29]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 901136-Chloropiperonyl chlorideHCID 13286893Ethyl 5-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

Produkt 1

HCID 700329105-Allyloxy-1-[(6-chlorobenzo[1,3]dioxol-5-yl)methyl]-1h-indole-2-carboxylic acid ethyl esterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553
Tetrabutylammonium Iodide
Katalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of NaH (60% suspension in mineral oil, 0.24 g, 6.12 mmol) and DMF (20 mL) was added 5-allyloxyindole-2-carboxylic acid ethyl ester (1.0 g, 4.08 mmol), from Example 1(d). After stirring at room temperature for 1 h, 6-chloropiperonyl chloride (0.84 g, 4.08 mmol) was added followed by the addition of tetrabutyl ammonium iodide (0.15 g, 0.41 mmol). The reaction was stirred at room temperature for 18 h. When the reaction was complete as indicated by TLC, the reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine and dried (Na2SO4). The solvent was removed in vacuo and the resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes) to yield the desired product as an oil (0.72 g, 43%). LC/MS (ES+) m/e 414.0 [M+H]+.

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature for 18 h
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customthe resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b1232f5cd63a4771b76d4c4fa67413d4
Quelldatensatz
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06670388B1

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