(z)-2-Ethoxy-3-(1h-indol-4-yl)-acrylic acid ethyl ester → Rac-2-ethoxy-3-(1h-indol-4-yl)-propionic acid ethyl ester

HRID 11381

Reaktionsgleichung

Reaktionsgleichung von HRID 11381
[CH2:1]([O:3][C:4](=[O:19])/[C:5](/[O:16][CH2:17][CH3:18])=[CH:6]/[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[CH3:2].[H][H]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)[CH3:2]

Komponenten

5

Edukt 2

HCID 69280560(z)-2-Ethoxy-3-(1h-indol-4-yl)-acrylic acid ethyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 69279879Rac-2-ethoxy-3-(1h-indol-4-yl)-propionic acid ethyl esterAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 15.0 g of (Z)-2-ethoxy-3-(1H-indol-4-yl)-acrylic acid ethyl ester in 250 ml of EtOH and 3.08 g of Pd/C (10%) was hydrogenated at 22° C. for 2 h, after which time hydrogen uptake ceased. The suspension was filtered, the filtrate evaporated and the residue chromatographed on silica gel (eluent: gradient of hexane and ethyl acetate) to give 12.28 g of the title compound as a light brown oil.

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. customthe filtrate evaporated
  3. customthe residue chromatographed on silica gel (eluent: gradient of hexane and ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-721817e573834a32927246bb40fe9b53
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098228B2

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