Benzonitrile → 2-(3-Methyl-5-isoxazolyl)-1-phenyl-1-ethanone

HRID 36945ノート

反応式

HRID 36945 の反応式
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.[O:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH2:13]([Li])[CH2:14][CH2:15]C.C(#N)C1C=CC=CC=1>CCCCCC>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][C:12]([C:11]2[CH:15]=[CH:14][CH:13]=[CH:9][CH:10]=2)=[O:8])[O:4][N:3]=1

参加物

6

反応物 4

HCID 7505BenzonitrileHCID 8028TetrahydrofuranHCID 93123,5-DimethylisoxazoleHCID 178418339Butyllithium

生成物 1

HCID 109545992-(3-Methyl-5-isoxazolyl)-1-phenyl-1-ethanone

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

The general procedure of Micetich, Can. J. Chem., 48, 2006 (1970) was employed. 3,5-Dimethylisoxazole (4.86 g, 50 mmol) and 100 mL of tetrahydrofuran were placed in a flask under nitrogen and cooled to -70° C. with an ether/Dry Ice bath. To this was added with cooling and stirring 20 mL (50 mmol) of 2.5M n-butyl lithium in hexane solution at a rate such that the temperature remained below -50° C. and the mixture was allowed to stir at -70° C. for 1 hr. Benzonitrile (5.67 g, 55 mmol) was then added and stirring at -70° C. was continued for an additional 2-hr period. The resulting mixture was allowed to warm to ambient temperature and was then concentrated by evaporation under reduced pressure. The residue was mixed with 100 mL of 1N hydrochloric acid and extracted with dichloromethane. The organic extract was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a solid residue which was recrystallized from ether to obtain 4.6 g (46 percent of theory) of the title compound as a yellow solid melting at 73°-74° C.

後処理

  1. additionTo this was added
  2. temperaturewith cooling
  3. customremained below -50° C.
  4. stirringstirring at -70° C.
  5. waitwas continued for an additional 2-hr period
  6. temperatureto warm to ambient temperature
  7. concentrationwas then concentrated by evaporation under reduced pressure
  8. additionThe residue was mixed with 100 mL of 1N hydrochloric acid
  9. extractionextracted with dichloromethane
  10. extractionThe organic extract
  11. dry with materialwas dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated by evaporation under reduced pressure
  14. customto obtain a solid residue which
  15. customwas recrystallized from ether

出典と根拠

ORDレコード
ord-b73d0e7469e54fc5b205306c4662845d
出典データセット
uspto-grants-1995_05
特許番号
US05418247

反応ノート

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