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

HRID 82415

반응식

HRID 82415 반응식
[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]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 86618950Ethyl 2-diazo-6-methyl-3-oxoheptanoate2회

생성물 1

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

시약·촉매·용매 2

HCID 168478Rhodium acetate촉매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5f74e315cb3b428d8833721a06b43084
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846681B2

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