Potassium Hydroxide → (1S*,5S*)-2,3,4,4-tetrachloro-1-ethoxymethyl-8-oxabicyclo[3.2.1]octa-2,6-diene

HRID 341656

Reaktionsgleichung

Reaktionsgleichung von HRID 341656
[Cl:1][CH:2]1[C:4](Cl)([Cl:5])[C:3]1([Cl:8])[Cl:7].[OH-].[K+].[CH2:11]([O:13][CH2:14][C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)[CH3:12]>O1CCOCC1>[Cl:5][C:4]1[C@:15]2([CH2:14][O:13][CH2:11][CH3:12])[O:16][C@H:17]([C:3]([Cl:8])([Cl:7])[C:2]=1[Cl:1])[CH:18]=[CH:19]2

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 22631PentachlorocyclopropaneHCID 80455Furfuryl ethyl ether

Produkt 1

HCID 68731449(1S*,5S*)-2,3,4,4-tetrachloro-1-ethoxymethyl-8-oxabicyclo[3.2.1]octa-2,6-dieneAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Pentachlorocyclopropane (25 g, 0.116 mol) is added to a suspension of potassium hydroxide (7.8 g, 0.139 mol) in 1,4-dioxane (900 ml) and the mixture is stirred at room temperature for 30 minutes and then heated to 65° C. for a further 30 minutes. 2-Ethoxymethylfuran (17.5 g, 0.139 mol) is added to the reaction mixture, the temperature is raised to 85-90° C. and the mixture is stirred for 16 hours. The reaction mixture is cooled to room temperature, filtered through a plug of diatomaceous earth and the filtrate is evaporated under reduced pressure to give (1S*,5S*)-2,3,4,4-tetrachloro-1-ethoxymethyl-8-oxabicyclo[3.2.1]octa-2,6-diene (23 g), used without further purification in the next step.

Aufarbeitung

  1. temperatureheated to 65° C. for a further 30 minutes
  2. temperaturethe temperature is raised to 85-90° C.
  3. stirringthe mixture is stirred for 16 hours
  4. temperatureThe reaction mixture is cooled to room temperature
  5. filtrationfiltered through a plug of diatomaceous earth
  6. customthe filtrate is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ce4415e0f8ec4e4e971c0f5ecaaf1cc4
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895761B2

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