Reaktion #1014179

Reaktionsgleichung

water

methyl cis-4-formylcyclohexane carboxylate

potassium tert-butoxide

Benzyltriphenylphosphonium bromide

→

title compound

Ausbeute 18.7%

Methyl cis-4-((E)-2-phenylvinyl)cyclohexane carboxylate

Ausbeute 18.7%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 1.6 hours at the same temperature
2. 2
   workup.STIRRINGit was stirred
3. 3
   Extraktionextracted with toluene
4. 4
   WaschenThe organic layer was washed with water and saturated brine in order
5. 5
   TrocknenAfter drying over anhydrous sodium sulfate
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   SonstigeThe residues were purified by silica gel column chromatography (9% ethyl acetate/hexane)

Vorschrift

Benzyltriphenylphosphonium bromide (2.94 g) was dissolved in THF (23.0 mL), added at −20° C. with potassium tert-butoxide (1.07 g) in small portions, and stirred for 1 hour at the same temperature. Subsequently, a THF (6.0 mL) solution of methyl cis-4-formylcyclohexane carboxylate (1.00 g) was added dropwise over 35 minutes, and stirred for 1.6 hours at the same temperature. After raising the temperature to room temperature, it was stirred after adding water and extracted with toluene. The organic layer was washed with water and saturated brine in order. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residues were purified by silica gel column chromatography (9% ethyl acetate/hexane) to obtain the title compound (268 mg) as a colorless oil.

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