Hydrochloric Acid → Methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate

HRID 45183

反応式

HRID 45183 の反応式
C[O:2][C:3](=O)[CH:4]=[CH2:5].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.C[O-:18].[Na+].Cl.[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>CO>[CH3:23][O:24][C:25]([CH:21]1[CH2:22][C:14]([C:15]#[N:16])([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:2])=[O:18]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 8028TetrahydrofuranHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 10942334Sodium Methoxide

生成物 1

HCID 12230235Methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

70 mL of methylacrylate and 50 g of 4-fluorophenylacetonitrile were dissolved in a mixture of 200 mL of THF and 50 mL of dry methanol. 150 mL of sodium methylate (30% in methanol) were added dropwise, while temperature was maintained below 40° C. The mixture was stirred at room temperature for 15 h and heated for another 4 h at 50° C. When the reaction was complete, the mixture was allowed to cool to room temperature and poured onto a cold 2N aqueous hydrochloric acid solution. The aqueous layer was extracted three times with ethyl acetate and the combined organic layer was washed with water and brine, dried over magnesium sulphate and evaporated to give 101.5 g of the desired product. Rt=1.59 min (Method 5). Detected mass: 276.2 (M+H+).

後処理

  1. temperaturewas maintained below 40° C
  2. temperatureheated for another 4 h at 50° C
  3. temperatureto cool to room temperature
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washthe combined organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

出典と根拠

ORDレコード
ord-436b0523c98649b0bbc1c57c86e622fd
出典データセット
uspto-grants-2013_09
特許番号
US08541449B2

関連ノート

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