Potassium Hydroxide → 1-[2-(p-Ethoxycarbonylphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole

HRID 1719380

Reaktionsgleichung

Reaktionsgleichung von HRID 1719380
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12]Cl)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[N:16]1([C:21]2[NH:22][C:23]3[C:28]([C:29]=2[CH3:30])=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:19][N:18]=[CH:17]1.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][N:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]([CH3:30])=[C:21]2[N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 3

HCID 14797Potassium HydroxideHCID 132808392-(1-Imidazolyl)-3-methylindoleHCID 13476653Ethyl 4-(2-chloroethoxy)benzoate

Produkt 1

HCID 202681801-[2-(p-Ethoxycarbonylphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysator2×HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(p-Ethoxycarbonylphenoxy)-1-chloroethane is added in one portion to a mixture of 2-(1-imidazolyl)-3-methylindole (1.97 g), potassium hydroxide (0.62 g) and tetrabutylammonium bromide (0.32 g) in acetonitrile (250 ml) while stirring under nitrogen at room temperature. After stirring at room temperature for 65 hours an additional 0.64 g of tetrabutylammonium bromide is added and the mixture is refluxed for 41 hours. The reaction mixture is cooled to room temperature and filtered. The filtrate is concentrated in vacuo and the oil obtained dissolved in ethyl acetate and extracted with 1N hydrochlorid acid. The aqueous extract is made basic to pH 10 with 3N sodium hydroxide and extracted with ethyl acetate (3×100 ml). This extract is dried over magnesium sulfate, filtered, and concentrated in vacuo to give a crude oil which is purified by flash chromatography on silica gel. The product is eluted with 3% methanol in methylene chloride to give 1-[2-(p-ethoxycarbonylphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole; NMR (CDCl3): δ 8.02 (d, 2H), 7.87-7.13 (m, 7H), 6.80 (d, 2H), 4.50-4.00 (m, 6H), 2.20 (s, 3H), 1.37 (t, 3H).

Aufarbeitung

  1. additionis added
  2. temperaturethe mixture is refluxed for 41 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe oil obtained
  7. extractionextracted with 1N hydrochlorid acid
  8. extractionThe aqueous extract
  9. extractionextracted with ethyl acetate (3×100 ml)
  10. dry with materialThis extract is dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto give a crude oil which
  14. customis purified by flash chromatography on silica gel
  15. washThe product is eluted with 3% methanol in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-c540622599954298ae01429536a30147
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04539410

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