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Methanol → 1-Cyclohexyl-3-ethoxy-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-ene

HRID 1165698
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1165698
[CH:1]1([CH:7]=[C:8]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:9]([OH:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:22](Br)[CH3:23].CO>O1CCOCC1>[CH:1]1([CH:7]=[C:8]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:9]([O:14][CH2:22][CH3:23])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 1148141-Cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol

Produkt 1

HCID 538447631-Cyclohexyl-3-ethoxy-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-eneAusbeute 37,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 26.3 g (0.1 mol) of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol (prepared as described in Example II-2) in 50 ml of dioxane was added dropwise to a suspension of 3 g of 80% strength sodium hydride in 100 ml of dioxane. After the addition had ended, the mixture was warmed to 50° C. for 1 hour. After the mixture had cooled, 10.9 g (0.1 mol) of ethyl bromide were added dropwise to it, and the reaction mixture was heated under reflux overnight. After the mixture had cooled, 10 ml of methanol were added to it and it was concentrated in a rotary evaporator. The residue was taken up in methylene chloride and was washed with water. After the organic phase had been dried over sodium sulphate, it was filtered and the filtrate was concentrated. The residue was distilled. 11.0 g (37.8% of theory) of 1-cyclohexyl-3-ethoxy-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent- 1-ene of boiling point 110° C./0.07 mm Hg were obtained.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureAfter the mixture had cooled
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux overnight
  5. temperatureAfter the mixture had cooled
  6. concentrationwas concentrated in a rotary evaporator
  7. washwas washed with water
  8. dry with materialAfter the organic phase had been dried over sodium sulphate, it
  9. filtrationwas filtered
  10. concentrationthe filtrate was concentrated
  11. distillationThe residue was distilled

Quellen und Nachweise

ORD-Eintrag
ord-289b24118523431d8e79f24712f4c4db
Quelldatensatz
uspto-grants-1990_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04911750

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