Hydrochloric Acid → Ethyl 2,2-dimethyl-5-oxocyclopentane-1-carboxylate

HRID 82415

Reaktionsgleichung

Reaktionsgleichung von HRID 82415
[N+](=[C:3]([C:9](=[O:15])[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].Cl>C(Cl)Cl.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH3:13][C:12]1([CH3:14])[CH2:11][CH2:10][C:9](=[O:15])[CH:3]1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 86618950Ethyl 2-diazo-6-methyl-3-oxoheptanoate2×

Produkt 1

HCID 67339971Ethyl 2,2-dimethyl-5-oxocyclopentane-1-carboxylateAusbeute 1.737,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 168478Rhodium acetateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Rhodium acetate (170 mg) was added to a solution of ethyl 2-diazo-6-methyl-3-oxoheptanoate (0.5 g) in DCM (80 mL). A solution of ethyl 2-diazo-6-methyl-3-oxoheptanoate (7.652 g) in DCM (50 mL) was added in portions. The mixture was stirred at room temperature for 1 hour. 1N HCl (100 mL) was added. The organic phase was separated. The aqueous phase was extracted with DCM (100 mL). The combined DCM solutions were dried (Na2SO4). After filtration and concentration, the crude material was purified with flash chromatography to give ethyl 2,2-dimethyl-5-oxocyclopentanecarboxylate (7.54 g). 1H NMR (CDCl3, 400 MHz) δ (ppm): 4.25-4.09 (m, 2H), 2.52-2.37 (m, 2H), 2.03-1.99 (m, 2H), 1.80-1.67 (m, 1H), 1.33-1.26 (m, 9H).

Aufarbeitung

  1. customThe organic phase was separated
  2. extractionThe aqueous phase was extracted with DCM (100 mL)
  3. dry with materialThe combined DCM solutions were dried (Na2SO4)
  4. filtrationAfter filtration and concentration
  5. customthe crude material was purified with flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5f74e315cb3b428d8833721a06b43084
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846681B2

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