Reaktion #814372

Reaktionsgleichung

8-ethynyl-1,4-dioxaspiro[4.5]decane

3,5-di(trifluoromethyl)phenyl iodide

triethylamine

→

4-[3,5-di(trifluoromethyl)phenylethynyl]cyclohexanone

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter this time the reaction mixture is concentrated under reduced pressure to a residue
2. 2
   workup.STIRRINGThe residue is then stirred for about 2 hours with 150 mL of aqueous 1N hydrochloric acid
3. 3
   ExtraktionAfter this time the mixture is extracted with three 100 mL portions of ethyl acetate
4. 4
   WaschenThe combined extracts are washed with an aqueous solution of 10% lithium chloride
5. 5
   TrocknenThe organic layer is dried with magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   EinengenThe filtrate is concentrated under reduced pressure

Vorschrift

A solution of 3.9 grams (0.022 mole) of 8-ethynyl-1,4-dioxaspiro[4.5]decane, 10.5 grams (0.031 mole) of 3,5-di(trifluoromethyl)phenyl iodide (prepared in Step A of this Example), 10.7 grams (0.077 mole) of triethylamine, 0.5 gram (catalyst) of bis(triphenylphosphine)palladium(II) chloride, and 0.5 gram (catalyst) of copper(I) iodide in 100 mL of acetonitrile is stirred at ambient temperature for about 18 hours. After this time the reaction mixture is concentrated under reduced pressure to a residue. The residue is then stirred for about 2 hours with 150 mL of aqueous 1N hydrochloric acid. After this time the mixture is extracted with three 100 mL portions of ethyl acetate. The combined extracts are washed with an aqueous solution of 10% lithium chloride. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 4-[3,5-di(trifluoromethyl)phenylethynyl]cyclohexanone.

Quelle