p-Toluenesulfonic acid → HCID 20394599, Verbindung

HRID 261633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 261633
C(OC([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)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH3:18][O:17][C:15]([CH2:14][CH:9]1[CH:8]([CH2:19][C:20]#[C:21][CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10]1)=[O:16]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 203065655-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

Produkt 1

HCID 20394599HCID 20394599, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A 800 mg quantity of 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone is dissolved in 50 ml of benzene, and 30 mg of p-toluenesulfonic acid is added to the solution. The mixture is refluxed for 30 minutes. The resulting reaction mixture is neutralized with sodium bicarbonate, and the solvent removed. The residue is purified by a silica gel column and distilled in a vacuum, giving 4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (3), R2 =CH3) in a yield of 93%, b.p. 102°-103° C./3 mm Hg.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 30 minutes
  2. customThe resulting reaction mixture
  3. customthe solvent removed
  4. customThe residue is purified by a silica gel column
  5. distillationdistilled in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-37c6b030506c405783bbd01c0af83635
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04166188

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