P-Toluenesulfonylhydrazide → 1,2-Di-(methoxycarbonyl)-4-ethylidene-cyclohexane

HRID 2165442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165442
[C:1]([C:4]1[CH2:5][CH:6]([C:14]([O:16][CH3:17])=[O:15])[CH:7]([CH2:12][CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])(=O)[CH3:2].S(NN)(C1C=CC(C)=CC=1)(=O)=O>C(O)C>[CH3:11][O:10][C:8]([CH:7]1[CH2:12][CH2:13][C:4](=[CH:1][CH3:2])[CH2:5][CH:6]1[C:14]([O:16][CH3:17])=[O:15])=[O:9]

Komponenten

4

Edukt 2

HCID 15303P-ToluenesulfonylhydrazideHCID 13453483Dimethyl 1,2,3,6-tetrahydro-4-acetyl-phthalate

Produkt 1

HCID 540253811,2-Di-(methoxycarbonyl)-4-ethylidene-cyclohexaneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

17 g of dimethyl 1,2,3,6-tetrahydro-4-acetyl-phthalate, prepared as described in Example 1, was refluxed in anhydrous ethanol with 14.6 g of tosylhydrazine. After removal of the solvent, 24 g of dimethyl 1,2,3,6-tetrahydro-4-(1-tosylhydrazono-ethyl)-phthalate (IV) crystallized from water: m.p. 162°-163° C m/z 408 (M+.). This compound was dissolved in chloroform, and treated at 0° C with 14 ml of catechol borane Sodium acetate was added to the reaction mixture, which was then refluxed. After washing with water, the solvent was evaporated off and the residue was purified by chromatography on a column of silica gel giving 10 g of the title compound (yield 80%): m/z 226 (M+.);

Aufarbeitung

  1. customAfter removal of the solvent, 24 g of dimethyl 1,2,3,6-tetrahydro-4-(1-tosylhydrazono-ethyl)-phthalate (IV)
  2. customcrystallized from water
  3. dissolutionThis compound was dissolved in chloroform
  4. additiontreated at 0° C with 14 ml of catechol borane Sodium acetate
  5. additionwas added to the reaction mixture, which
  6. temperaturewas then refluxed
  7. washAfter washing with water
  8. customthe solvent was evaporated off

Quellen und Nachweise

ORD-Eintrag
ord-cc8b86a068e5429687e5d0257c5534f1
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04939282

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