Ethanol → Benzenebutanenitrile, beta-oxo-alpha-(3-(trifluoromethyl)phenyl)-

HRID 1589093ノート

反応式

HRID 1589093 の反応式
[Na].C(O)C.[F:5][C:6]([F:17])([F:16])[C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1.[C:18]1([CH2:24][C:25](OCC)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[F:5][C:6]([F:16])([F:17])[C:7]1[CH:8]=[C:9]([CH:13]([C:25]([CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])[C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1

参加物

6

反応物 4

HCID 702EthanolHCID 7590Ethyl phenylacetateHCID 75360m-TrifluoromethylphenylacetonitrileHCID 5360545Sodium2 回

生成物 1

HCID 106559Benzenebutanenitrile, beta-oxo-alpha-(3-(trifluoromethyl)phenyl)-収率 73.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

In this example, 4.91 g of metallic sodium was added to 110 ml of anhydrous ethanol at room temperature and stirred until all of the sodium dissolved. A mixture containing 18.76 g of (3-trifluoromethylphenyl)acetonitrile and 21.73 g of ethyl phenylacetate was then added dropwise and the resulting mixture was stirred at reflux for about 18 hours. The mixture was then poured into 300 ml water and extracted three times with ethyl ether. The pH of the extracted aqueous layer was adjusted to a pH of about 1 with aqueous 10 wt. % hydrochloric acid and again extracted three times with ethyl ether. The organic layer was washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated to dryness under vacuum affording 22.6 g of the title compound.

後処理

  1. dissolutiondissolved
  2. additionwas then added dropwise
  3. temperatureat reflux for about 18 hours
  4. extractionextracted three times with ethyl ether
  5. extractionagain extracted three times with ethyl ether
  6. washThe organic layer was washed twice with saturated aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness under vacuum

出典と根拠

ORDレコード
ord-49605d1b4eb54723b0e3d3e2e958f459
出典データセット
uspto-grants-1986_02
特許番号
US04568376

反応ノート

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