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

HRID 82415

反応式

HRID 82415 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 168478Rhodium acetate触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5f74e315cb3b428d8833721a06b43084
出典データセット
uspto-grants-2014_09
特許番号
US08846681B2

関連ノート

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