Ethyl 2-thiopheneglyoxylate → [(3-Methyl-butyl)-hydrazono]-thiophen-2-yl-acetic acid ethyl ester

HRID 30977

Reaktionsgleichung

Reaktionsgleichung von HRID 30977
[CH2:1]([O:3][C:4](=[O:12])[C:5](=O)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH3:2].[CH3:13][CH:14]([CH3:19])[CH2:15][CH2:16][NH:17][NH2:18]>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5](=[N:18][NH:17][CH2:16][CH2:15][CH:14]([CH3:19])[CH3:13])[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 77693Ethyl 2-thiopheneglyoxylateHCID 18696583(3-Methylbutyl)hydrazine

Produkt 1

HCID 72562995[(3-Methyl-butyl)-hydrazono]-thiophen-2-yl-acetic acid ethyl esterAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of oxo-thiophen-2-yl-acetic acid ethyl ester (1d) (3.97 g, 21.6 mmol) in absolute ethanol (100 mL), (3-Methyl-butyl)-hydrazine (2b) (2.0 g, 19.6 mmol) was added. The mixture was stirred at 80° C. under N2 atmosphere for 2-25 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel to give the desired product (3d) (2.48 g) that was directly used in the next step. LC-MS (ESI+): m/e 269.2 [M+1]+, 537.4 [2M+1]+, 559.0 [2M+Na]+ (exact ms: 268.12).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-87f0c78e6581409aafe2d4313913c391
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425552B2

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