Cyclooctanone → Methyl 2-oxocyclooctane-1-carboxylate

HRID 521404

Reaktionsgleichung

Reaktionsgleichung von HRID 521404
[C:1](=[O:6])([O:4][CH3:5])OC.[H-].[Na+].[C:9]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C([O-])(O)=O.[Na+]>C1COCC1>[O:17]=[C:9]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:1]([O:4][CH3:5])=[O:6]

Komponenten

6

Edukt 4

HCID 10403CyclooctanoneHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 227411Methyl 2-oxocyclooctane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of dimethyl carbonate (30 mL, 0.36 mol) in dry THF (600 mL) was added sodium hydride (15 g, 0.36 mol) by portion at 5-10° C. The resulting mixture was stirred at this temperature for 30 min and then was added a solution of cyclooctanone (15.0 g, 0.12 mol) in THF (100 mL) dropwise over 30 min. The resultant mixture was stirred at refluxed for 4 h before cooling to room temperature. The reaction mixture was poured into saturated NaHCO3 solution (100 mL) and ice (500 g), and then the mixture was extracted with PE/EA (4:1, 400 mL×2). The organic layer was washed with brine (400 mL), dried over Na2SO4 and concentrated to give crude product. Then the target product (19.3 g, 88%) was purified by distilling at 60° C. in vacuum.

Aufarbeitung

  1. temperatureat refluxed for 4 h
  2. extractionthe mixture was extracted with PE/EA (4:1, 400 mL×2)
  3. washThe organic layer was washed with brine (400 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThen the target product (19.3 g, 88%) was purified
  8. distillationby distilling at 60° C. in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a410fe6f8f614e1fa924503e0f07019a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328111B2

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