5-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone → HCID 70583183, Verbindung

HRID 972105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972105
[C:1]([O:5][C:6]([C:8]1([CH2:19][C:20]#[C:21][CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[C:1]([O:5][C:6]([C:8]1([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 203065655-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone2×HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 70583183HCID 70583183, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

A 4.5 g quantity of 5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (1-a)) is dissolved in a mixture of 50 ml of n-hexhane and 50 ml of acetone, and 7 g of a Lindlar catalyst is added to the solution. Hydrogen gas is introduced into the solution with stirring. The reaction is completed when the solution has absorbed the theoretical amount of the gas. On completion of the reaction, the catalyst is filtered off from the reaction mixture, and the filtrate is concentrated at reduced pressure. The residue is distilled in a vacuum, affording 5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone (compound (1-b), R1 =CH3, R2 =CH3) in a yield of 99.8%, b.p. 81°-85° C./0.005 mm Hg.

Aufarbeitung

  1. additionis added to the solution
  2. customhas absorbed the theoretical amount of the gas
  3. customOn completion of the reaction
  4. filtrationthe catalyst is filtered off from the reaction mixture
  5. concentrationthe filtrate is concentrated at reduced pressure
  6. distillationThe residue is distilled in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-77e64be8590c4661a8ca87e679fa5f32
Quelldatensatz
uspto-grants-1979_07
Patentnummer
US04163111

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