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

HRID 1913268

反応式

HRID 1913268 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 21911973Ethyl 1-methyl-4-oxocyclohexanecarboxylate収率 101.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-05e4d28d91c34094b81f567dce02b417
出典データセット
uspto-grants-2013_12
特許番号
US08609675B2

関連ノート

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