Ethyl orthoformate → (E)-3-(4-chloro-3-trifluoromethyl-styryl)-1,2,4-oxadiazole

HRID 1491968ノート

反応式

HRID 1491968 の反応式
[Cl:1][C:2]1[CH:13]=[CH:12][C:5](/[CH:6]=[CH:7]/[C:8](=[N:10][OH:11])[NH2:9])=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].[CH:18](OCC)(OCC)OCC>B(F)(F)F.CCOCC>[Cl:1][C:2]1[CH:13]=[CH:12][C:5](/[CH:6]=[CH:7]/[C:8]2[N:9]=[CH:18][O:11][N:10]=2)=[CH:4][C:3]=1[C:14]([F:15])([F:16])[F:17]

参加物

4

反応物 2

HCID 31214Ethyl orthoformateHCID 86748304(E)-4-chloro-3-trifluoromethyl-cinnamamide oxime

生成物 1

HCID 23364566(E)-3-(4-chloro-3-trifluoromethyl-styryl)-1,2,4-oxadiazole収率 71%

試薬・触媒・溶媒 1

HCID 8000Boron trifluoride etherate触媒

実験手順

5.2 g (0.02 mol) of (E)-4-chloro-3-trifluoromethyl-cinnamamide oxime are introduced into 50 ml of triethyl orthoformate and 2 drops of boron trifluoride etherate are added at room temperature. The mixture is then stirred for 2 hours at reflux temperature and the entire batch is concentrated in vacuo. The residue is taken up in 100 ml of methylene chloride and washed in succession with 100 ml of 2N hydrochloric acid, saturated sodium carbonate solution and water. The organic phase is dried over sodium sulphate and the solvent is subsequently distilled off. 3.9 g (71.0% of theory) of (E)-3-(4-chloro-3-trifluoromethyl-styryl)-1,2,4-oxadiazole are obtained.

後処理

  1. additionare added at room temperature
  2. temperatureat reflux temperature
  3. concentrationthe entire batch is concentrated in vacuo
  4. washwashed in succession with 100 ml of 2N hydrochloric acid, saturated sodium carbonate solution and water
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. distillationthe solvent is subsequently distilled off

出典と根拠

ORDレコード
ord-26b40f4176154b0597afba6c376cc1e9
出典データセット
uspto-grants-1994_12
特許番号
US05371231

反応ノート

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