Isopropanol → 2-(Diisopropylamino)ethyl 2-phenylbenzofuran-7-carboxylate

HRID 1761914

Reaktionsgleichung

Reaktionsgleichung von HRID 1761914
[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH:20]([N:23]([CH:27]([CH3:29])[CH3:28])[CH2:24][CH2:25]Cl)([CH3:22])[CH3:21].[OH-].[K+].C(O)(C)C>O.C(OCC)(=O)C>[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([O:18][CH2:25][CH2:24][N:23]([CH:27]([CH3:29])[CH3:28])[CH:20]([CH3:22])[CH3:21])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 142297062-Phenylbenzofuran-7-carboxylic acid

Produkt 1

HCID 142297672-(Diisopropylamino)ethyl 2-phenylbenzofuran-7-carboxylateAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1.16 g of 2-phenylbenzofuran-7-carboxylic acid, 1.0 g of 2-(diisopropylamino)ethyl chloride hydrochloride, 0.66 g of potassium hydroxide and 20 ml of isopropanol is refluxed for 1 hour. After cooling, ethyl acetate and water are added to the reaction mixture. The organic layer is collected, washed with a saturated sodium chloride solution and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=20:1) to give 1.51 g 2-(diisopropylamino)ethyl 2-phenylbenzofuran-7-carboxylate as colorless oil.

Aufarbeitung

  1. temperatureis refluxed for 1 hour
  2. temperatureAfter cooling
  3. customThe organic layer is collected
  4. washwashed with a saturated sodium chloride solution
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-3db9825a54ae4ac6bd36322a9eaf447b
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04829067

Verknüpfte Notizen

Wird geladen…