[F:1]/[C:2](/[Si](CC)(CC)CC)=[C:3](/[F:13])\[CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH3:12])[CH2:6][CH2:5]1.O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(OC)(C)C>[F:13]/[C:3](/[CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH3:12])[CH2:6][CH2:5]1)=[CH:2]/[F:1]34.6 g (0.11 mol) of [(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane are refluxed for 20 h in 900 ml of THF together with 45 ml of water and 160 ml of TBAF (0.16 mol, 1 M soln. in THF). The batch is diluted with MTBE and washed a number of times with water. The aqueous phases are extracted with MTBE, and the combined organic phases are washed with water and saturated sodium chloride solution. The solution is dried using sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (SiO2, pentane), giving 1-((E)-1,2-difluorovinyl)-4-propylcyclohexane as a colourless oil.
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