Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate → Ethyl 1-methyl-4-oxocyclohexanecarboxylate

HRID 1913268

반응식

HRID 1913268 반응식
[CH3:1][C:2]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.[N+]([O-])([O-])=O.[Ce].[NH4+]>C(#N)C.O>[CH3:1][C:2]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3][CH2:4][C:5](=[O:6])[CH2:10][CH2:11]1

참가 물질

5

반응물 2

HCID 19004805Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylateHCID 57418452Ammonium cerium-nitrate

생성물 1

HCID 21911973Ethyl 1-methyl-4-oxocyclohexanecarboxylate수율 101.8%

시약·촉매·용매 2

HCID 962Water용매3회HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (Int-18b, 2.09 g, 9.17 mmol) was dissolved in acetonitrile (100 mL) and water (50 mL). Ammonium cerium nitrate (503 mg, 0.92 mmol) in water (50 mL) was added and the resulting mixture was heated up to 70° C. and stirred for 1 h. After being cooled down to room temperature, water (100 mL) was added and the mixture was extracted with ether (100 mL×3). The combined organics were washed with water, brine and dried. After concentration, the residue was purified on a column (silica gel, 0-30% ethyl acetate in hexane) which gave ethyl 1-methyl-4-oxocyclohexanecarboxylate (Int-18c) (1.72 g) as an oil.

후처리

  1. temperatureAfter being cooled down to room temperature
  2. extractionthe mixture was extracted with ether (100 mL×3)
  3. washThe combined organics were washed with water, brine
  4. customdried
  5. concentrationAfter concentration
  6. customthe residue was purified on a column (silica gel, 0-30% ethyl acetate in hexane) which

출처 및 근거

ORD 기록
ord-05e4d28d91c34094b81f567dce02b417
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609675B2

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