反応 #1014179

反応方程式

water

methyl cis-4-formylcyclohexane carboxylate

potassium tert-butoxide

Benzyltriphenylphosphonium bromide

→

title compound

収率 18.7%

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

収率 18.7%

溶媒

THF

THF

反応条件

後処理

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

実験手順

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.

出典