Methyl propiolate → HCID 178498875, Verbindung

HRID 235968

Reaktionsgleichung

Reaktionsgleichung von HRID 235968
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](=[N:15]O)[NH2:14])=[CH:11][CH:10]=1>CO>[C:1]([C:2]1[N:14]=[C:13]([C:12]2[CH:17]=[CH:18][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[NH:15][CH:3]=1)([O:5][CH3:6])=[O:4]

Komponenten

4

Edukt 2

HCID 13536Methyl propiolateHCID 21471p-Methoxybenzamidoxime

Produkt 1

HCID 178498875HCID 178498875, VerbindungAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl propiolate (25.4 g, 0.3 mol), p-methoxybenzamidoxime (50 g, 0.3 mol) and CH3OH (700 ml) was heated at reflux with stirring. After 8 hours, the reaction mixture was concentrated to dryness, and the residue treated with diphenyl ether (300 ml) and heated at reflux. After 2.5 hours, the reaction mixture was poured in C6H14 (2 L) and allowed to stand. The C6H14 was decanted off and the residue chromatographed on silica gel. The product was eluted with 2% CH3OH--CHCl3 to yield 21 g (30%) of 63; m.p. 188°-90° C. (trituration with Et2O).

Aufarbeitung

  1. temperatureat reflux
  2. concentrationthe reaction mixture was concentrated to dryness
  3. additionthe residue treated with diphenyl ether (300 ml)
  4. temperatureheated
  5. temperatureat reflux
  6. waitAfter 2.5 hours
  7. additionthe reaction mixture was poured in C6H14 (2 L)
  8. customThe C6H14 was decanted off
  9. customthe residue chromatographed on silica gel
  10. washThe product was eluted with 2% CH3OH

Quellen und Nachweise

ORD-Eintrag
ord-ebf15d41f84e419a8d76a1acaf410486
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642311

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