Methyl 4-acetyl-4-tert-butoxycarbonyl-3-formyl-6-nonynoate → 5-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

HRID 46546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46546
[C:1]([C:4]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH2:13][C:14]#[C:15][CH2:16][CH3:17])[CH:5]([CH:11]=O)[CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]>C1C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[C:21]([O:20][C:18]([C:4]1([CH2:13][C:14]#[C:15][CH2:16][CH3:17])[C:1](=[O:3])[CH:2]=[CH:11][CH:5]1[CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Komponenten

5

Edukt 1

HCID 53669204Methyl 4-acetyl-4-tert-butoxycarbonyl-3-formyl-6-nonynoate

Produkt 1

HCID 203065655-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 241BenzeneLösungsmittelHCID 8082PiperidineLösungsmittel

Versuchsvorschrift

A 790 mg quantity of the compound (7) obtained above is dissolved in 50 ml of benzene containing 1 ml of acetic acid and 1 ml of piperidine, and the solution is refluxed for 4 hours. On completion of the reaction, the solvent is removed, and the residue dissolved in ethyl acetate. The solution is washed with water and an aqueous solution of sodium bicarbonate and thereafter dried. The residue is distilled in a vacuum, giving 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (2-a), R1 =t-Bu, R2 =CH3) in a yield of 78%, b.p. 82°-86° C./0.006 mm Hg.

Aufarbeitung

  1. temperaturethe solution is refluxed for 4 hours
  2. customOn completion of the reaction
  3. customthe solvent is removed
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe solution is washed with water
  6. dry with materialan aqueous solution of sodium bicarbonate and thereafter dried
  7. distillationThe residue is distilled in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-312e7788dcf44f87908cc15390fccea2
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173707

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