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

HRID 1198735

Reaktionsgleichung

Reaktionsgleichung von HRID 1198735
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9ca5b263c137492bad1e89096fe24021
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281719

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