Quinoline → 1,6-Dicarbomethoxy-cis-3-hexene

HRID 1613000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613000
[C:1]([CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])([O:3][CH3:4])=[O:2].N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[C:11]([CH2:10][CH2:9]/[CH:8]=[CH:7]\[CH2:6][CH2:5][C:1]([O:3][CH3:4])=[O:2])([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 2

HCID 7047QuinolineHCID 109545171,6-Dicarbomethoxy-3-hexyne

Produkt 1

HCID 232729831,6-Dicarbomethoxy-cis-3-hexeneAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1,6-dicarbomethoxy-3-hexyne [II-1] (5 g), a Lindlar catalyst (5% Pd-CaCO3 -PbO) (50 mg), quinoline (25 mg) and methanol (15 ml) is charged in an atmospheric hydrogenation apparatus and subjected to reduction at room temperature under atmospheric pressure. After completion of the reaction, the catalyst is removed by filtration and the filtrate is concentrated to give 1,6-dicarbomethoxy-cis-3-hexene [II-2] (4.70 g, yield; 93.0%), b.p. 92°-95° C./0.3 mmHg.

Aufarbeitung

  1. customsubjected to reduction at room temperature under atmospheric pressure
  2. customAfter completion of the reaction
  3. customthe catalyst is removed by filtration
  4. concentrationthe filtrate is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-cd04e879614c41f980684f008036c460
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05191109

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