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

HRID 1675895

Reaction equation

HRID 1675895 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 67339971Ethyl 2,2-dimethyl-5-oxocyclopentane-1-carboxylateYield 1,737.3%

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-27dd36c817924445b17a4cb07fbbf45e
Source dataset
uspto-grants-2011_08
Patent number
US08003651B2

Linked notes

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