3-Methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol → a Methyl jasmonate

HRID 1732438

Reaktionsgleichung

Reaktionsgleichung von HRID 1732438
[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([OH:11])[CH:7]1[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16])=[O:4]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH:7]1[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16])=[O:4]

Komponenten

3

Edukt 1

HCID 100595943-Methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

Produkt 1

HCID 5319693a Methyl jasmonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
18 °C

Versuchsvorschrift

A 150 mg quantity of 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol is dissolved in 10 ml of methylene chloride. A 2 ml quantity of chromic acid solution of 2 M concentration is added dropwise to the solution. The mixture is stirred at about 18° C. for 12 hours and thereafter extracted with ethyl acetate. The extract is washed with aqueous solution of sodium chloride, dried and concentrated. The residue is purified with a silica gel column and distilled in a vacuum, affording 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanone (compound (4), R2 =CH3) in a yield of 88%, b.p. 92°-96° C./2.7 mm Hg.

Aufarbeitung

  1. concentrationA 2 ml quantity of chromic acid solution of 2 M concentration
  2. additionis added dropwise to the solution
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with aqueous solution of sodium chloride
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is purified with a silica gel column
  8. distillationdistilled in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-067fa63bb80d4e94acebb1b91ba3278b
Quelldatensatz
uspto-grants-1980_12
Patentnummer
US04237308

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