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

HRID 1613000Notes

Reaction equation

HRID 1613000 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 232729831,6-Dicarbomethoxy-cis-3-hexeneYield 93.1%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cd04e879614c41f980684f008036c460
Source dataset
uspto-grants-1993_03
Patent number
US05191109

Reaction notes

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