Methanol → p-Chloro-0-[1,2-bis(trifluoromethyl)vinyl]acetophenone oxime

HRID 484231

反応式

HRID 484231 の反応式
[F:1][C:2]([F:10])([F:9])[C:3]#[C:4][C:5]([F:8])([F:7])[F:6].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[N:20][OH:21])[CH3:19])=[CH:14][CH:13]=1.CO.CC(C)([O-])C.[K+]>O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[N:20][OH:21])[CH3:19])=[C:16]([C:4]([C:5]([F:8])([F:7])[F:6])=[CH:3][C:2]([F:10])([F:9])[F:1])[CH:17]=1

参加物

6

反応物 4

HCID 887MethanolHCID 69654Hexafluoro-2-butyneHCID 96172p-Chloroacetophenone oximeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 131717584p-Chloro-0-[1,2-bis(trifluoromethyl)vinyl]acetophenone oxime

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Hexafluoro-2-butyne is slowly bubbled through a 55°-60° C. solution of p-chloroacetophenone oxime (17.0 g, 0.10 mol), methanol (80 mL) and potassium tert-butoxide (1.12 g, 0.01 mol) over a 5 hour period. The solvent is removed in vacuo to obtain a liquid which is poured into water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give an oil. The oil is chromatographed using silica gel and eluted with 1% ethylacetate in methylene chloride to 5% ethyl acetate in methylene chloride to give p-chloro-0-[1,2-bis(trifluoromethyl)vinyl]acetophenone oxime, vinyl-(Z) as a yellow liquid (21.5 g, 65%) and 2-(p-chlorophenyl)-4,5-trans-bis(trifluoromethyl)-1-pyrrolin-5-ol as a white solid (2.35 g, mp 152.5°-153° C., 7%).

後処理

  1. customThe solvent is removed in vacuo
  2. customto obtain a liquid which
  3. extractionextracted with ether
  4. washThe combined organic extracts are washed sequentially with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customThe oil is chromatographed
  9. washeluted with 1% ethylacetate in methylene chloride to 5% ethyl acetate in methylene chloride

出典と根拠

ORDレコード
ord-8d5d1b80327f474fac12a48de13f6ca9
出典データセット
uspto-grants-1993_07
特許番号
US05229524

関連ノート

読み込み中…