Methyl iodide → Ethyl 1-methyl-2-oxocyclopentane-1-carboxylate

HRID 530235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530235
[C:1](=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH2:16][CH3:17])=[O:14].CI>CC(C)=O>[CH3:1][C:9]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10][CH2:11][CH2:12][C:8]1=[O:7]

Komponenten

5

Edukt 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Produkt 1

HCID 227353Ethyl 1-methyl-2-oxocyclopentane-1-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred suspension of dry potassium carbonate (16.64 g, 120.4 mmol) in dry acetone (200 mL) under argon was added ethyl 2-oxocyclopentanecarboxylate (9.40 g, 60.2 mmol) followed by methyl iodide (7.5 mL, 120.4 mmol). The reaction was heated to reflux for 3 hours and then another portion of methyl iodide (7.5 mL, 120.4 mmol) was added and the reaction was refluxed overnight. The reaction mixture was cooled and then filtered through a silica gel pad and the solid was washed with acetone (100 mL×3). The organic phase was concentrated under reduced pressure and the residue dispersed in acetone (200 mL) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=100/1->50/1) to afford the title compound as a colorless liquid (8.35 g, Yield: 82%). 1H NMR (400 MHz, CDCl3) δ 4.22-4.10 (m, 2H), 2.57-2.40 (m, 2H), 2.36-2.27 (m, 1H), 2.11-2.00 (m, 1H), 1.98-1.83 (m, 2H), 1.31 (s, 3H), 1.25 (t, J=7.0 Hz, 3H) ppm.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. temperaturethe reaction was refluxed overnight
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered through a silica gel pad
  6. washthe solid was washed with acetone (100 mL×3)
  7. concentrationThe organic phase was concentrated under reduced pressure
  8. additionthe residue dispersed in acetone (200 mL)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=100/1->50/1)

Quellen und Nachweise

ORD-Eintrag
ord-962d8357b66f4a4482aa69baca161838
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353063B2

Notizen zur Reaktion

Wird geladen…