Acetone → 3-(3,4-Dimethoxyphenyl)-2-methyl-6-oxohexane-3-carbonitrile

HRID 405015ノート

反応式

HRID 405015 の反応式
[C:1]([OH:6])(=O)[C:2](O)=O.[C:7]([C:9]1([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)OC(CCC(C)C)CO1)#[N:8].[C:29](=O)([O-])[O-].[K+].[K+].[CH3:35][C:36]([CH3:38])=O>O>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:9]([CH:36]([CH3:38])[CH3:35])([CH2:29][CH2:2][CH:1]=[O:6])[C:7]#[N:8])[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

参加物

6

反応物 4

HCID 180AcetoneHCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 671041742-Cyano-2-(3,4-dimethoxyphenyl)-2-isopropylethyl-1,3-dioxolane

生成物 1

HCID 30153703-(3,4-Dimethoxyphenyl)-2-methyl-6-oxohexane-3-carbonitrile

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

Oxalic acid dehydrate (504.6 mg, 3.96 mmol) was added to a solution of the acetal (19) (372 mg, 1.16 mmol) in acetone (10 mL) and water (10 mL). The resulting mixture was stirred at 80° C. for four hours. The reaction mixture was cooled to room temperature. Potassium carbonate (1.3 g) was added to quench the reaction. The mixture was extracted with ethyl ether (3×20 mL). The organic solution was washed with brine, dried over sodium sulfate, concentrated to afford the crude product (17) (293 mg), which was used in the next step without further purification. The product was confirmed by 1H-NMR spectra.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl ether (3×20 mL)
  5. washThe organic solution was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-8e15abe2e51e4aeaa373318080326d13
出典データセット
uspto-grants-2014_06
特許番号
US08748648B2

反応ノート

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