Cyclooctanone → Ethyl 2-oxocyclononanecarboxylate

HRID 5389

Reaktionsgleichung

Reaktionsgleichung von HRID 5389
[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.C([O+](CC)CC)C.[N+](=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N-]>C(Cl)Cl>[CH2:28]([O:27][C:25]([CH:24]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:1]1=[O:9])=[O:26])[CH3:29]

Komponenten

5

Edukt 3

HCID 10403CyclooctanoneHCID 12192Ethyl diazoacetateHCID 2723982Triethyloxonium tetrafluoroborate

Produkt 1

HCID 107210Ethyl 2-oxocyclononanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Cyclooctanone (25 g, 198 mmol) is dissolved in methylene chloride (500 mL) and the solution is cooled to 0° C. Triethyloxonium tetrafluoroborate (121.6 g, 640 mmol) is added. Ethyl diazoacetate (41.61 g, 365 mmol) is then added dropwise over 25 minutes, and the reaction is stirred at 0° C. for 4 hours. The reaction is quenched by pouring into a solution of sodium bicarbonate (160 g) in water (1.6 L) and stirring overnight. The reaction mixture is then extracted several times with methylene chloride, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by vacuum distillation (0.2-1.0 mm Hg) and the fraction boiling between 100°-125° C. is collected to give 2-ethoxycarbonyl-cyclononanone.

Aufarbeitung

  1. customThe reaction is quenched
  2. additionby pouring into a solution of sodium bicarbonate (160 g) in water (1.6 L)
  3. stirringstirring overnight
  4. extractionThe reaction mixture is then extracted several times with methylene chloride
  5. dry with materialthe combined organic layers are dried (Na2SO4)
  6. customthe solvent is evaporated
  7. distillationThe product is purified by vacuum distillation (0.2-1.0 mm Hg)
  8. customboiling between 100°-125° C.
  9. customis collected

Quellen und Nachweise

ORD-Eintrag
ord-e3905ec671db4476912df221b80d4a05
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244889

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