Ethyl Acrylate → 4-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-cyclohex-3-enecarboxylic Acid Ethyl Ester

Participants

Reaction Steps

To a slurry of aluminum chloride (0.1 equi) in toluene (1 mL/mmole), ethyl acrylate (1 equi.) (1 equi.) was added at ice temperature. The reaction mixture was stirred at ice temperature for 10 min. Then a solution 2-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-buta-1,3-diene (40) (0.5M in THF) (1 equi.) was added at ice temperature over a period of 20 min. The reaction mixture was stirred at ice temperature for 10 h, water, extracted with hexane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (hexanes) gave 4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-cyclohex-3-enecarboxylic acid ethyl ester (41) as a colorless oil (88%).

Provenance & Evidence