Hydrochloric Acid → 2-(4-Tert-butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile

HRID 230090

反応式

HRID 230090 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][N:15]1[C:19]([Cl:20])=[C:18]([C:21](Cl)=[O:22])[C:17]([Cl:24])=[N:16]1.CC(C)([O-])C.[K+].Cl>C1COCC1.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11](=[C:21]([C:18]2[C:17]([Cl:24])=[N:16][N:15]([CH3:14])[C:19]=2[Cl:20])[OH:22])[C:12]#[N:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 76784(4-tert-Butylphenyl)acetonitrileHCID 221694993,5-Dichloro-1-methylpyrazole-4-carbonyl chlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 570994822-(4-Tert-butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile収率 31.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1.00 g of 4-tert-butylphenylacetonitrile and 1.23 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride were dissolved in 20 ml of THF, and 1.01 g of potassium t-butoxide was added thereto with cooling with ice. After the resulting mixture was stirred overnight at room temperature, water was added thereto, acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried with sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was dissolved in a mixed solvent of 10 ml of water and 10 ml of dioxane, and 0.38 g of potassium hydroxide was added thereto and heated under reflux for 4 hours. After having been left to be at room temperature, this was acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 0.64 g of 2-(4-tert-butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile from the fraction eluted with n-hexane:ethyl acetate=2:1.

後処理

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried with sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe residual product was dissolved in a mixed solvent of 10 ml of water and 10 ml of dioxane, and 0.38 g of potassium hydroxide
  7. additionwas added
  8. temperatureheated
  9. temperatureunder reflux for 4 hours
  10. waitAfter having been left
  11. customto be at room temperature
  12. extractionextracted with ethyl acetate
  13. washThe organic layer was washed with water
  14. dry with materialdried over sodium sulfate
  15. distillationthe solvent was distilled off under reduced pressure
  16. customThe residual product was purified through silica gel column chromatography

出典と根拠

ORDレコード
ord-e4cbc42825364f7b825d596cc8ef4189
出典データセット
uspto-grants-2009_07
特許番号
US07566683B2

関連ノート

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