Ethyl 2-oxocyclopentanecarboxylate → HCID 68937923, Verbindung

HRID 576272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576272
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].N([O-])=[O:11].[Na+].[C:14]([O-])(=O)[CH3:15].[K+].[O:19]=[C:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(O)C.Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]2[C:3]=1[NH:4][C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:22]2[CH2:23][CH2:24][C:20]([O:19][CH2:14][CH3:15])=[O:11]

Komponenten

7

Edukt 4

HCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 517044Potassium AcetateHCID 27733172-Bromo-5-fluoroanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 68937923HCID 68937923, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2-bromo-5-fluoroaniline (5 g) in ethanol (17.5 ml) and 1.6M HCl (50 mL) at −5° C. was treated with 2.5M NaNO2 (10.5 ml). 4.5M potassium acetate (29.2 ml) was then added, followed by ethyl 2-oxocyclopentanecarboxylate (3.8 ml). The reaction mixture was stirred at 0° C. for 15 minutes, warmed to 20° C. over 1.5 hours, extracted with dichloromethane, concentrated and dried in vacuo. The residue was dissolved in 67 ml of (H2SO4/ethanol, 17:50), refluxed for 2 days, cooled to room temperature, quenched with water and extracted with dichloromethane. The combined extracts were washed with brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel with 5-20% ethyl acetate in hexanes. The product was purified further by trituration with ethanol.

Aufarbeitung

  1. temperaturewarmed to 20° C. over 1.5 hours
  2. extractionextracted with dichloromethane
  3. concentrationconcentrated
  4. customdried in vacuo
  5. dissolutionThe residue was dissolved in 67 ml of (H2SO4/ethanol, 17:50)
  6. temperaturerefluxed for 2 days
  7. temperaturecooled to room temperature
  8. customquenched with water
  9. extractionextracted with dichloromethane
  10. washThe combined extracts were washed with brine
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe concentrate was purified by column chromatography on silica gel with 5-20% ethyl acetate in hexanes
  15. customThe product was purified further by trituration with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0981ded673f8423dbdda1d0dd0fc96fa
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035047B2

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