Ethanol → N-(6-Methylhept-5-en-3-ylidene)hydroxylamine

HRID 1165086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165086
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=CC=C[CH:2]=1.C(O)=O.C([N:25]([CH2:28][CH3:29])CC)C.[OH2:30].[CH2:31](Cl)Cl.[CH2:34](O)[CH3:35]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:2][C:1](=[CH:34][CH2:35][C:28](=[N:25][OH:30])[CH2:29][CH3:31])[CH3:6]

Komponenten

7

Edukt 5

HCID 702Ethanol2×HCID 962WaterHCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 11084032Triethylammonium formate

Produkt 1

HCID 71334023N-(6-Methylhept-5-en-3-ylidene)hydroxylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

An aliquot (0.5 mole) of the resultinge compound was reacted under stirring for 1 hour together with 0.005 mole of palladium acetate, 0.02 mole of tripenylphosphine, 1.5 moles of triethylamine formate, 20 moles of ethanol and 12 moles of water. After the reaction, ethanol was evaporated from the reaction mixture under reduced pressure. Ten moles of methylene chloride was added to the residue, and the mixture was washed with water. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 2-methyl-5-hydroxyimino-2-heptene in a yield of 96 mole %. A quantitative analysis of the reaction mixture by gas chromatography showed that the reaction proceeded quantitatively.

Aufarbeitung

  1. customwas evaporated from the reaction mixture under reduced pressure
  2. washthe mixture was washed with water
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-920fba8d918a4666a4d5ed7354e03fca
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04906768

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