Tetrabutylammonium Fluoride → (e)-1-Fluoro-4-tosyloxy-2-butene
Reaction equation
[S:1]([O:11][CH2:12]/[CH:13]=[CH:14]/[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-:44]>C1COCC1>[F:44][CH2:15]/[CH:14]=[CH:13]/[CH2:12][O:11][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (E)-1,4-ditosyloxy-2-butene (256 mg, 0.64 mmol) in 10 mL of THF was added Bu4NF (0.7 mL, 1M in THF, 0.7 mmol). The mixture was heated to reflux for 30 min. Evaporation and purification of the residue by flash column chromatography with hexane:ether/2:1 afforded the product as a colorless oil (60 mg, 38%). 1 H NMR (CDCl3, 300 MHz) δ 7.80 (d, J=8.4 Hz, 2H), 7.36 (d, J=8.4 Hz, 2H), 5.99-5.75 (m, 2H, 4.84 (ddd, JFCH=46.5 Hz, J=4.8, 1.2 Hz, 2H), 4.59-4.56 (m, 2H), 2.46 (s, 3H).