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

HRID 1675895

Reaktionsgleichung

Reaktionsgleichung von HRID 1675895
[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-27dd36c817924445b17a4cb07fbbf45e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003651B2

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